多组分反应构建杂环化合物的合成研究
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摘要
多组分反应是将多个底物放在一个反应器中，不经过中间体的分离，一步构建产物的操作方法。由于其具有操作简单、反应连续、原子经济性等优点而满足有机合成、药物合成的需要而受到广泛关注。本论文采用多组分反应的合成方法，设计合成一些可能具有药物活性的含氮、含氧和含硫杂环化合物。论文首先综述了近年来国内外多组分反应在合成杂环化合物方面的应用，简要介绍本论文的研究内容、研究目的和意义，以及本论文多组分操作的方法。
本论文主要研究了二苯乙酮、芳醛和脲(或者碳酸胍)三组分无溶剂反应，一步构建了具有较大空间位阻嘧啶化合物。同时使用芳醛、2-吡啶乙酮和碳酸胍（或者氰基胍）合成部分含氮的多齿配体化合物；第四部分研究以2,4-噻唑烷-二酮、芳醛、丙二腈和正丁胺(或者环丙胺、3-吡啶甲胺)为反应底物，不需要使用任何催化剂，四组分反应有效、方便的一步构建5-氨基噻吩衍生物，这是一条不同于传统的Gewald反应合成噻吩的新方法。反应中发现2,4-噻唑烷-二酮发生了开环反应参与了噻吩结构的形成。实验结果表明反应对不同结构的胺具有良好的适应性；此外，研究了2-噻吩甲酰三氟丙酮、芳醛、达米酮和醋酸铵四组分反应方便的合成一系列新的喹啉衍生物(含有1,4-二氢吡啶核)。同时研究了2-噻吩甲酰三氟丙酮、芳醛和脲合成含有噻吩基的嘧啶衍生物，这是对Biginelli反应新的发展，本操作方法选择性好，底物适应范围广，较易构建化合物库；在第六部分研究了无溶剂条件下芳醛、四氢萘酮和环己酮的三组分反应有效的合成含氧杂环化合物呫吨醇，在简单操作下合成结构复杂的化合物说明了多组分反应的有效性，这些化合物都是首次报道的。同时意外发现芳醛和芳酮五组分反应合成环己醇衍生物的途径，这是合成环己醇反应新的发展，对合成的机理给以详细解析；最后，以活性化合物丙二腈参与的多组分反应合成吡啶化合物，也获得仔细研究，反应中意外获得了四氢化萘化合物，同时研究了异喹啉化合物的有效合成，本文为这几类化合物的合成研究提供了新的合成路线。
研究表明，多组分反应是合成含氮、含氧和含硫杂环化合物的有效的方法。特别对于一些结构复杂的杂环化合物合成尤其如此。研究中发现无溶剂反应对多组分反应合成杂环化合物是一个有力的途径。每个系列都合成大量化合物，可以非常容易的构建小分子杂环化合物库。论文共合成139个化合物，绝大多数为首次合成的结构。所有产物都通过红外、核磁和高分辨质谱等分析手段对化合物的结构进行了详细的表征。部分化合物的晶体结构分析进一步确证的化合物结构。论文对每个系列化合物的的合成提出了可能的反应机理。所有研究的反应都具有反应操作简便、条件温和、反应时间短、产率高、以及原子经济等诸多优点。
Multicomponent reaction (MCR) is the one-pot method for the synthesis of compoundsby taking many substrates into a reactor without separating intermediate products. Becauseof its simple operation, continuous reaction, atom economy, and meeting the need oforganic and pharmaceutical synthesis, this method has brought the much attention of people.In this dissertation, we designed and prepared some containing nitrogen, oxygen and sulfurheterocyclic compounds using multicomponent reactions. At first, the recent review ofsynthesis heterocyclic compounds using multicomponent reaction at home and abroad wasintroduced. The contents, purpose, significance and the operation of multicomponentreaction experiments about this dissertation were also involved in this part.
The larger steric hindrance pyrimidines have been synthetized by one-potmulticomponent reaction of1,2-diphenylethanone, aromatic aldehydes and urea (orguanidine carbonate) under solvent-free conditions. At the same time, somenitrogen-containing polydentate ligands have been prepared from the raction of aromaticaldehydes,1-(pyridin-2-yl)ethanone and guanidine carbonate (or cyanoguanidine). In partfour, an efficient and convenient method for the preparation of5-amino-dihydrothiophenederivatives by four-component reaction of thiazolidine-2,4-dione, aromatic aldehyde,malononitrile and n-butylamine (or cyclopropanamine, pyridin-3-ylmethanamine) withoutusing any other catalysts was reported. It was found that the thiazolidine-2,4-dione byopening its ring to take part in constructing thiophene derivatives. This is a new process forsynthesis of thiophene derivatives with good adaptability about the different structures ofthe amines, and is different from classical the Gewald reaction. Furthermore, a series of newtype kuinoline derivatives (containing1,4-dihydropyridines core) were synthetized byfour-component reaction of4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione, aromaticaldehyde,5,5-dimethylcyclohexane-1,3-dione (dimedonecas) and ammonium acetatewithout using any catalysts under room temperature. Simultaneously, containing-thienylpyrimidine derivatives were synthetized from4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione, aromatic aldehyde and urea, and this is the new development of Biginellireaction. The advantages of these processes are good selectivity, broad substrate scope, easyconstruction of compounds libraries. In part six, the containing oxygen heterocycliccompounds, xanthydrol derivatives were efficiently prepared by the three-componentreaction of aromatic aldehyde,3,4-dihydronaphthalen-1(2H)-one, and cyclohexanone undersolvent-free conditions. It shows the effectiveness of multicomponent reaction for the synthesis of these complex structures with a very simple operation. The products ofxanthydrol were the first reported. We find an unexpected way to synthesize cyclohexanolderivatives from five-component reaction, and this is the new development for synthesis ofthese compounds. At last, the pyridine compounds have been synthetized viamulticomponent reaction by malononitrile taking part in the reaction, and the unexpectedtetrahydronaphthalene derivatives have been obtained in our research. At the same time, wereported the efficient method for synthesis of isoquinoline derivatives. There are all newprocesses for synthesis of these compounds.
The results of the experiment show that multicomponent reaction is an efficient methodfor constructing of nitrogen-containing, oxygen-containin and sulfur-containingheterocyclic compounds. Especially, it may be the best method for constructing somecomplex heterocyclic compounds. Becaue of synthetizing many compounds for each series,there would very easy to constructing small molecule heterocyclic compounds libraries. Inthis dissertation,139compounds have been synthesized and most of them were reported forthe first time. All the structures of the products were confirmed on the basis of IR,1H NMRspectra, and highresolution mass spectrometry (HRMS), and some compounds wereadditionally confirmed by X-ray diffraction analysis. The possible reaction mechanismswere proposed in the text. The advantages of these reported reactions are simple operation,mild reaction conditions, short reaction time, high yields, and atomic economy.
本论文主要研究了二苯乙酮、芳醛和脲(或者碳酸胍)三组分无溶剂反应，一步构建了具有较大空间位阻嘧啶化合物。同时使用芳醛、2-吡啶乙酮和碳酸胍（或者氰基胍）合成部分含氮的多齿配体化合物；第四部分研究以2,4-噻唑烷-二酮、芳醛、丙二腈和正丁胺(或者环丙胺、3-吡啶甲胺)为反应底物，不需要使用任何催化剂，四组分反应有效、方便的一步构建5-氨基噻吩衍生物，这是一条不同于传统的Gewald反应合成噻吩的新方法。反应中发现2,4-噻唑烷-二酮发生了开环反应参与了噻吩结构的形成。实验结果表明反应对不同结构的胺具有良好的适应性；此外，研究了2-噻吩甲酰三氟丙酮、芳醛、达米酮和醋酸铵四组分反应方便的合成一系列新的喹啉衍生物(含有1,4-二氢吡啶核)。同时研究了2-噻吩甲酰三氟丙酮、芳醛和脲合成含有噻吩基的嘧啶衍生物，这是对Biginelli反应新的发展，本操作方法选择性好，底物适应范围广，较易构建化合物库；在第六部分研究了无溶剂条件下芳醛、四氢萘酮和环己酮的三组分反应有效的合成含氧杂环化合物呫吨醇，在简单操作下合成结构复杂的化合物说明了多组分反应的有效性，这些化合物都是首次报道的。同时意外发现芳醛和芳酮五组分反应合成环己醇衍生物的途径，这是合成环己醇反应新的发展，对合成的机理给以详细解析；最后，以活性化合物丙二腈参与的多组分反应合成吡啶化合物，也获得仔细研究，反应中意外获得了四氢化萘化合物，同时研究了异喹啉化合物的有效合成，本文为这几类化合物的合成研究提供了新的合成路线。
研究表明，多组分反应是合成含氮、含氧和含硫杂环化合物的有效的方法。特别对于一些结构复杂的杂环化合物合成尤其如此。研究中发现无溶剂反应对多组分反应合成杂环化合物是一个有力的途径。每个系列都合成大量化合物，可以非常容易的构建小分子杂环化合物库。论文共合成139个化合物，绝大多数为首次合成的结构。所有产物都通过红外、核磁和高分辨质谱等分析手段对化合物的结构进行了详细的表征。部分化合物的晶体结构分析进一步确证的化合物结构。论文对每个系列化合物的的合成提出了可能的反应机理。所有研究的反应都具有反应操作简便、条件温和、反应时间短、产率高、以及原子经济等诸多优点。
Multicomponent reaction (MCR) is the one-pot method for the synthesis of compoundsby taking many substrates into a reactor without separating intermediate products. Becauseof its simple operation, continuous reaction, atom economy, and meeting the need oforganic and pharmaceutical synthesis, this method has brought the much attention of people.In this dissertation, we designed and prepared some containing nitrogen, oxygen and sulfurheterocyclic compounds using multicomponent reactions. At first, the recent review ofsynthesis heterocyclic compounds using multicomponent reaction at home and abroad wasintroduced. The contents, purpose, significance and the operation of multicomponentreaction experiments about this dissertation were also involved in this part.
The larger steric hindrance pyrimidines have been synthetized by one-potmulticomponent reaction of1,2-diphenylethanone, aromatic aldehydes and urea (orguanidine carbonate) under solvent-free conditions. At the same time, somenitrogen-containing polydentate ligands have been prepared from the raction of aromaticaldehydes,1-(pyridin-2-yl)ethanone and guanidine carbonate (or cyanoguanidine). In partfour, an efficient and convenient method for the preparation of5-amino-dihydrothiophenederivatives by four-component reaction of thiazolidine-2,4-dione, aromatic aldehyde,malononitrile and n-butylamine (or cyclopropanamine, pyridin-3-ylmethanamine) withoutusing any other catalysts was reported. It was found that the thiazolidine-2,4-dione byopening its ring to take part in constructing thiophene derivatives. This is a new process forsynthesis of thiophene derivatives with good adaptability about the different structures ofthe amines, and is different from classical the Gewald reaction. Furthermore, a series of newtype kuinoline derivatives (containing1,4-dihydropyridines core) were synthetized byfour-component reaction of4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione, aromaticaldehyde,5,5-dimethylcyclohexane-1,3-dione (dimedonecas) and ammonium acetatewithout using any catalysts under room temperature. Simultaneously, containing-thienylpyrimidine derivatives were synthetized from4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione, aromatic aldehyde and urea, and this is the new development of Biginellireaction. The advantages of these processes are good selectivity, broad substrate scope, easyconstruction of compounds libraries. In part six, the containing oxygen heterocycliccompounds, xanthydrol derivatives were efficiently prepared by the three-componentreaction of aromatic aldehyde,3,4-dihydronaphthalen-1(2H)-one, and cyclohexanone undersolvent-free conditions. It shows the effectiveness of multicomponent reaction for the synthesis of these complex structures with a very simple operation. The products ofxanthydrol were the first reported. We find an unexpected way to synthesize cyclohexanolderivatives from five-component reaction, and this is the new development for synthesis ofthese compounds. At last, the pyridine compounds have been synthetized viamulticomponent reaction by malononitrile taking part in the reaction, and the unexpectedtetrahydronaphthalene derivatives have been obtained in our research. At the same time, wereported the efficient method for synthesis of isoquinoline derivatives. There are all newprocesses for synthesis of these compounds.
The results of the experiment show that multicomponent reaction is an efficient methodfor constructing of nitrogen-containing, oxygen-containin and sulfur-containingheterocyclic compounds. Especially, it may be the best method for constructing somecomplex heterocyclic compounds. Becaue of synthetizing many compounds for each series,there would very easy to constructing small molecule heterocyclic compounds libraries. Inthis dissertation,139compounds have been synthesized and most of them were reported forthe first time. All the structures of the products were confirmed on the basis of IR,1H NMRspectra, and highresolution mass spectrometry (HRMS), and some compounds wereadditionally confirmed by X-ray diffraction analysis. The possible reaction mechanismswere proposed in the text. The advantages of these reported reactions are simple operation,mild reaction conditions, short reaction time, high yields, and atomic economy.
引文
[1]邬端斌.有机化学[M].北京：科学出版社，2009：214-235.
[2] Zhu, S. F., Xie, J. B., Zhang, Y. Z., Li, S.,Zhou, Q. L. Well-Defined Chiral SpiroIridium/Phosphine-Oxazoline Cationic Complexes for Highly Enantioselective Hydrogenation ofImines at Ambient Pressure[J]. Journal of the American Chemical Society,2006,128(39):12886-12891.
[3] Niu, R., Xiao, J., Liang, T., Li, X. W. Facile Synthesis of Azaarene-Substituted3-Hydroxy-2-oxindoles via Br nsted Acid Catalyzed sp3C-H Functionalization[J]. Organic Letter,2012,3(124):676-679.
[4] Narayan, R., Fro hlich, R., Wu rthwein, E. U. Synthesis of Pyrroles through a4π-ElectrocyclicRing-Closure Reaction of1-Azapentadienyl Cations[J]. The Journal of Organic Chemistry,2012,77(4):1868-1879.
[5] Wang, Q. F., Song, X. K., Chen, J., Yan, C. G. Pyridinium Ylide-Assisted One-Pot Two-Step TandemSynthesis of Polysubstituted Cyclopropanes[J]. Journal of Combinatorial Chemistry,2009,11(6):1007-1010.
[6] Wang, H. J., Mo, L. P., Zhang, Z. H. Cerium Ammonium Nitrate-Catalyzed Multicomponent Reactionfor Efficient Synthesis of Functionalized Tetrahydropyridines[J]. Combinatorial Science,2011,13(2):181-185.
[7] Tan, D. S., Foley, M. A., Shair, M. D., Schreiber, S. L. Stereoselective Synthesis of over Two MillionCompounds Having Structural Features Both Reminiscent of Natural Products and Compatible withMiniaturized Cell-Based Assays[J]. Journal of the American Chemical Society,1998,120(33):8565-8566.
[8] Schreiber, S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery[J]. Science,2000,287(5460):1964-1969.
[9] Short, P. Ernest Guenther Award in the Chemistry of Natural Products[J]. Chemical&EngineeringNews,2003,81(3):51-52.
[10] Lee, D., Sello, J. K., Schreiber, S. L. Pairwise Use of Complexity-Generating Reactions inDiversity-Oriented Organic Synthesis[J]. Organic letters,2000,2(5):709-712.
[11] Burke, M. D., Schreiber, S. L. A planning strategy for diversity-oriented synthesis[J]. AngewandteChemie International Edition,2004,43(1):46-58.
[12]李明，郭维斯，文利荣，左正泉.三组分―一锅煮‖合成4,5-二氢吡唑并[1,5-a]嘧啶[J].有机化学,2008,28:472-475.
[13] Strecker, A. Ueber die künstliche Bildung der Milchs ure und einen neuen, dem Glycocollhomologen K rper[J]. Liebigs Annalen der Chemie,1850,75(1):27-45.
[14] Hantzsch, A. Ueber die Synthese pyridinartiger Verbindungen aus Acetessig ther undAldehydammoniak[J]. Liebigs Annalen der Chemie,1882,215(1):1-82.
[15] Radziszewski, B. Ueber die Constitution des Lophins und verwandter Verbindungen[J]. Berichte derdeutschen chemischen Gesellschaft,1882,15(2):1493-1496.
[16] Biginelli, P. Ueber Aldehyduramide des Acetessig thers[J]. Berichte der deutschen chemischenGesellschaft,1891,24(2):1317-1319.
[17] Mannich, C., Krosche, W. Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak undAntipyrin[J]. Archiv der Pharmazie,1912,250(1):647-667.
[18] Passerini, M., Isonitriles, I. Compound of p-isonitrileazobenzene with acetone and acetic acid[J].Gazzetta Chimica Italiana,1921,51(II),126-129.
[19] Ugi, I., Mey, R., Fetzer, U., Steinbruckner, C. Versuche mit Isonitrilen[J]. Angewandte ChemieInternational Edition,1959,71:386.
[20] Divanfard, H. R., Lysenko, Z., Wang, P. C., Joullie, M. M. An International Journal for RapidCommunication of Synthetic Organic Chemistry[J]. Synthetic Communications,1978,8(4):269-273.
[21] Weber, L., Wallbaum, S., Broger, C., et al. Optimierung der bilogischen aktivitaet yonkombinatorischen verbindungsbibliotheken durch einen genetischen algorithmus[J]. AngewandteChemie International,1995,(107):2452-2454.
[22] Keating, T. A., Armstrong, R. W. Molecular Diversity via a Convertible Isocyanide in the UgiFour-Component Condensation[J]. Journal of the American Chemical Society,1995,117(29):7842-7843.
[23] a. Barry, B. T., Dennis, G. H. Natural Product Synthesis Using Multicomponent ReactionStrategies[J]. Chemical Reviews,2009,109(9):4439-4486. b. Alexander, D. Recent Developmentsin Isocyanide Based Multicomponent Reactions in Applied Chemistry[J]. Chemical Reviews,2006,106(1):17-89.
[24] Bienayme, H., Hulme, C., Oddon, G., Schmitt, P. Maximizing synthetic efficiency: Multi-componenttransformations lead the way[J]. Chemistry-A European Journal,2000,8(16):3321-3329.
[25] Hantzsch, A. Neu Bildungsweise von Pyrrolderivaten[J]. Berichte der deutschen chemischenGesellschaft,1890,23(1):1474-1476.
[26] Khalili, B., Jajarmi, P., Eftekhari-Sis, B., Hashemi, M. M. Novel One-Pot, Three-ComponentSynthesis of New2-Alkyl-5-aryl-(1H)-pyrrole-4-ol in Water[J]. The Journal of Organic Chemistry,2008,76(3):2090-2095.
[27] Sakhno, Y. I., Desenko, S. M., Shishkina, S. V.; Shishkin, O. V., Sysoyev, D. O., Groth, U., Kappe, C.O., Chebanov, V. A. Multicomponent cyclocondensation reactions of minoazoles, arylpyruvicacids and aldehydes with controlled chemoselectivity[J]. Tetrahedron,2008,64(49):11041-11049.
[28] Attanasi, Q. A., Favi, G., Mantellini, F., Moscatelli, G., Santeusanio, S. Synthesis of FunctionalizedPyrroles via Catalyst-and Solvent-Free Sequential Three-Component Enamine AzoeneAnnulation[J]. The Journal of Organic Chemistry,2011,76(8):2860-2866.
[29] Galliford, C. V., Scheidt, K. A. Catalytic Multicomponent Reactions for the Synthesis of N-ArylTrisubstituted Pyrroles[J]. The Journal of Organic Chemistry,2007,72(5):1811-1813.
[30] Frolova, L. V., Evdokimov, N. M., Hayden, K., Malik, I., Rogelj, S., Kornienko, A., Magedov, I. V.One-Pot Multicomponent Synthesis of Diversely Substituted2-Aminopyrroles. A Short GeneralSynthesis of Rigidins A, B, C, and D[J]. Organic Letters,2011,13(5):1118-1121.
[31] Safari, J., Khalili, S. D., Rezaei, M., Banitaba, S. H., Meshkani, F. Nanocrystalline magnesiumoxide: a novel and efficient catalyst for facile synthesis of2,4,5-trisubstituted imidazolederivatives[J]. Monatshefte fuer Chemie,2010,141(12):1339-1345.
[32] Bahrami, K., Khodaei, M. M., Nejati, A. One-pot synthesis of1,2,4,5-tetrasubstituted and2,4,5-trisubstituted imidazoles by zinc oxide as efficient and reusable catalyst[J]. Monatshefte fuerChemie,2011,142(2):159-162.
[33] Mamedov, V. A., Zhukova, M. A., Beschastnova, T. N., Gubaidullin, A. T., Rakov, D. V. A simpleand efficient method for the synthesis of highly substituted imidazoles using3-aroylquinoxalin-2(1H)-ones[J]. Tetrahedron Letters,2011,52(33):4280-428.
[34] Siamaki, A. R., Arndtsen, B. A. A Direct One Step Synthesis of Imidazoles from Imines and AcidChlorides: A Palladium Catalyzed Multicomponent Coupling Approach[J]. Journal of the AmericanChemical Society,2006,128(18):6050-6051.
[35] Guchhait, S. K., Chandgude, A. L., Priyadarshani, G. CuSO4Glucose for in Situ Generation ofControlled Cu(I) Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehydewith Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles[J]. The Journal ofOrganic Chemistry,2012,77(9):4438-4444.
[36] Robin, S. B., Van, V. B., Nanda, E. S., Rob, F. S., Kanter, D., Frans, J. J., Christian, V. S.,Marcel, S.,Matthias, B. F., Marinus, B. G., Romano, V. A. O. Multicomponent synthesis of2-imidazolines[J].The Journal of Organic Chemistry,2005,70(9):3542-3553.
[37] Powner, M. W., Zheng, S. L., Szostak, J. W. Multicomponent Assembly of Proposed DNAPrecursors in Water[J]. Journal of the American Chemical Society,2012,134(33):13889-13895.
[38] Alinezhad, H., Tajbakhsh, M., Zare, M. Catalyst-free one-pot synthesis of1,4,5-trisubstitutedpyrazoles in2,2,2-trifluoroethanol[J]. Journal of Fluorine Chemistry,2011,132(11):995-1000.
[39] Adib, M., Sayahi, M. H., Rahbari, S. Reactions between isocyanides and dialkylacetylenedicarboxylates in the presence of1,2-diacylhydrazines.One-pot synthesis of highlyfunctionalized pyrazoles[J]. Tetrahedron Letters,2005,46(38):6545-6547.
[40] Muravyova, E. A., Desenko, S. M., Rudenko, R. V., Shishkina, S. V., Shishkin, O. V., Sen’ko, Y. V.,Vashchenko, E. V., Chebanov, V. A. Switchable selectivity in multicomponent heterocyclizations ofacetoacetamides, aldehydes,and3-amino-1,2,4-triazoles/5-aminopyrazoles[J]. Tetrahedron,2011,41(2):9389-9400.
[41] Dandia, A., Laxkar, A. K., Singh, R. New multicomponent domino reaction on water:highlydiastereoselective synthesis of spiro[indoline-3,4’-pyrazolo[3,4-b]pyridines]catalyzed by NaCl[J].Tetrahedron Letter,2012,53(24):3012–3017.
[42] Shaabani, A., Sarvary, A., Rezayan, A. H., Keshipour, S. Synthesis of fully substitutedpyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides[J]. Tetrahedron,2009,65(17):3492-3495.
[43] Valentin, A. C., Vyacheslav, E. S., Sergey, M. D., Vitaliy, N. C., Svetlana, V. S., Oleg, V. S., Kiril,M. K., Oliver, K. C. One-Pot Multicomponent Route to Pyrazoloquinolizinones[J]. Organic Letters,2007,9(9):1691-1694.
[44] Chen, Z. Y., Wu, J. Efficient Generation of Biologically Active H-Pyrazolo[5,1-a]isoquinolines viaMulticomponent Reaction[J]. Organic Letters,2010,12(21):4856–4859.
[45] Hantzsch, A. Condensationprodukte aus Aldehydammoniak und Ketoniartigen Verbindungen[J].Chemische Berichte,1881,14:1637-1638.
[46] Xia, J. J., Wang, G. W. One-Pot Synthesis and Aromatization of1,4-Dihydropyridines in RefluxingWater[J]. Synthesis,2005,14:2379-2383.
[47] Knoevenagel, E., Fries, A. Synthesen in der Pyridinreihe. Ueber eine Erweiterung derHantzsch'schen Dihydropyridinsynthese[J]. Berichte der deutschen chemischen Gesellschaft,1898,31(1):761-767.
[48] Khan, A. T.,Lal, M.,Khan, M. M. Synthesis of highly functionalized piperidines by one-potmulticomponent reaction using tetrabutylammonium tribromide (TBATB)[J]. Tetrahedron Letter.2010,51(33):4419-4424.
[49] Liu, W. B., Jiang, H. F., Zhu, S. F., Wang, W. Hydroalkylation leading to heterocycliccompounds(Part2): practical synthesis of polysubstituted1,2,3,4-tetrahydropyridines throughmulticomponent reactions(MCRs)[J]. Tetrahedron,2009,65(38):7985-7988.
[50] Sridhar, M., Ramanaiah, B. C., Narsaiah, C., Mahesh, B., Kumaraswamy, M., Mallu, K. K. R.,Ankathi, V. M., Rao, P. S. Novel ZnCl2-catalyzed one-pot multicomponent synthesis of2-amino-3,5-dicarbonitrile-6-thio-pyridines[J]. Tetrahedron Letter.2009,50(27):3897-3900.
[51] Evdokimov, N. M., Kireev, A. S., Yakovenko, A. A., Yu. M., Magedov, A. I. V., Kornienko, A.One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reactionof Malononitrile with Aldehydes and Thiols[J]. The Journal of Organic Chemistry.2007,72(9):3443-3453.
[52] Li, M., Zuo, Z. G., Wen, L. R., Wang, S.W. Microwave-Assisted Combinatorial Synthesis ofHexa-Substituted1,4-Dihydropyridines Scaffolds Using One-Pot Two-Step MulticomponentReaction followed by a S-Alkylation[J]. Journal of Combinatorial Chemistry,2008,10(3):436-441.
[53] Abu, T. K., Tasneem, P., Lokman, H. C. Effects of Substituents in the-Position of1,3-DicarbonylCompounds in Bromodimethylsulfonium Bromide-Catalyzed Multicomponent Reactions: A FacileAccess to Functionalized Piperidines[J]. The Journal of Organic Chemistry,2008,73(21):8398-8402.
[54] Biginelli, P. Ueber Aldehyduramide des Acetessigaethers[J]. Berichte der Deutschen ChemischenGesellschaft,1891,24:1317-1319.
[55] Pourmousavi, S. A., Hasani, M. H2SO4-Silica Catalyzed One-Pot and Efficient Synthesis ofDihydropyrimidinones Under Solvent-Free Conditions[J]. E-Journal of Chemistry,2011,8(1):462-466.
[56] Lei, M., Ma, L., Hu, L. H. Cu(ClO4)2·6H2O as an efficient catalyst for the synthesis of3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions[J]. Synthetic Communications,2011,41(20):3071-3077.
[57] Madhusudana, R. B. M., Pasha, M. A. Iodine-catalyzed versatile synthesis of4,6-diarylpyrimidin-2(1H)-ones (DAPMs) via one-pot, multicomponent reaction[J]. SyntheticCommunications,2011,41(13):1875-1880.
[58]彭家建，邓友全.室温离子液体催经―一锅法‖合成3，4-二氢嘧啶-2-酮[J]，有机化学，2002，22（1）：71.
[59] Valentin, A., Chebanov, Elena, A., Muravyova, S. M., Desenko, et al. Microwave-AssistedThree-Component Synthesis7-Aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and Their Selective Reduction[J]. Journal of Combinatorial Chemistry,2006,(3):427-434.
[60] Hulme, R., Zamora, O. D. P., Mota, E. J., Pasten, M. A., Contreras-Rojas, R., Miranda, R.,Valencia-Hernandez, I., Correa-Basurto, J., Trujillo-Ferrara, J., Delgado, F. Cyanamide:a convenientbuilding block to synthesize4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via amulticomponent reaction[J]. Tetrahedron,2008,64(15):3372-3380.
[61] Shaabani, A., Seyyedhamzeh, M., Maleki, A., Hajishaabanha, F. Diketene as an alternative substratefor a new Biginelli-like multicomponent reaction: one-pot synthesis of5-carboxamide substituted3,4-dihydropyrimidine-2(1H)ones[J]. Tetrahedron,2010,66(23):4040-4042.
[62] Chebil, E., Touil, S. Behaviour of β-keto--carbethoxyphosphonates and phosphine oxides in thebiginelli multicomponent reaction: regioselective synthesis of5-carbethoxy-6-phosphono-methyl-3,4-dihydropyrimidin-2-ones[J]. Heterocycles,2012,85(11):2765-2774.
[63] Zhang, M., Jiang, H. F., Liu, H. L., Zhu, Q. H. Convenient One-Pot Synthesis of MultisubstitutedTetrahydropyrimidines via Catalyst-Free Multicomponent Reactions[J]. Organic Letters,2007,9(21):4111-4113.
[64] Kumar, R., Raghuvanshi, K., Verma, R. K., Singh, M. S. Application of cyclic-1,3-diketones indomino and multicomponent reactions: facile route to highly functionalizedchromeno[2,3-d]pyrimidinones and diazabenzo[b]fluorenones under solvent-free conditions[J].Tetrahedron Letter,2010,51(45):5933-5936.
[65] Majumder, S., Gipson, K. R., Odom, A. L. A Multicomponent Coupling Sequence for Direct Accessto Substituted Quinolines[J]. Organic Letters,2009,11(20):4720-4723.
[66] Shindoh, N., Tokuyama, H., Takemoto, Y., Takasu, K. Auto-Tandem Catalysis in the Synthesis ofSubstituted Quinolines from Aldimines and Electron-Rich Olefins: Cascade Povarov-Hydrogen-Transfer Reaction[J]. The Journal of Organic Chemistry,2008,73(19):7451-7456.
[67] Guchhait, S. K., Jadeja, K., Madaan, G. A new process of multicomponent Povarov reaction–aerobicdehydrogenation: synthesis of polysubstituted quinolines[J]. Tetrahedron Letters,2009,50(49):6861-6865.
[68] Kadutskii, A. P., Kozlov, N. G., Pashkovskii, F. S. Synthesis of benzo [f] quinoline derivatives bythree-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde[J].Russian Journal of Organic Chemistry,2009,45(3):399-403.
[69] Song, S. J., Shan, Z. X., Jin, Y. One–pot synthesis of hexahydroquinolines via Hantzschfour-component reaction catalyzed by a cheap amino alcohol[J]. Synthetic Communications,2010,40(20):3067-3077.
[70] Nezhad, A. K., Sarikhani, S., Shahidzadeh, E. S., Panahi, F. L-Proline-promoted three-componentreaction of anilines, aldehydes and barbituric acids/malononitrile: regioselective synthesis of5-arylpyrimido-[4,5-b]quinoline-diones and2-amino-4-arylquinoline-3-carbonitriles in water[J].Green Chemistry,2012,14(10):2876-2884.
[71] Ding, Q. P., Wu, J. Lewis Acid-and Organocatalyst-Cocatalyzed Multicomponent Reactions of2-Alkynylbenzaldehydes, Amines, and Ketones[J]. Organic Letters,2007,9(24):4959-4962.
[72] Gao, K., Wu, J. Synthesis of Functionalized1,2-Dihydroisoquinolines via Multicomponent One-PotReaction of2-Alkynylbenzaldehyde, Amine, Zinc, and Allylic Bromide or Benzyl Bromide[J]. TheJournal of Organic Chemistry,2007,72(9):8611-8613.
[73] Heravi, M. M., Sadjad, S., Mokhtari, H. N., Oskooie, H. A., Shoar, R. H., Bamoharram, F. F. Anovel multi-component synthesis of4-arylaminoquinazolines[J]. Tetrahedron Letters,2009,50(8):943-945.
[74] Devi, N. S., Singh, S. J., Singh, O. M. An Efficient One-Pot Multicomponent Synthesis of2,3-Dihydro-3-alkyl/aryl-2-thioxoquinazolin-4(1H)-ones under Solvent-Free Conditions[J]. Synlett,2012,23(14):2111-2115.
[75] Shang,Y. J., Ju, K., He, X. W., Hu, J. S., Yu, S.Y., Zhang, M., Liao, K. S., Wang, L. F., Zhang, P.Copper-Catalyzed Multicomponent Reaction: Synthesis of4-Arylsulfonylimino-4,5-dihydrofuranDerivatives[J]. The Journal of Organic Chemistry,2010,75(16):5743–5745.
[76] Sun, C., Ji, S. J., Liu, Y. Facile synthesis of3-(2-furanyl)indoles via a multicomponent reaction[J],Tetrahedron Letter,2007,48(51):8987-8989.
[77] Shaabani, A., Rezayan, A. H., Ghasemi, S., Sarvary, A. A mild and efficient method for the synthesisof2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylates via an isocyanide-based multicomponentreaction[J]. Tetrahedron Letter,2009,50(13):1456-1458.
[78] Ma, C., Yang, Y. W. Thiazolium-Mediated Multicomponent Reactions: A Facile Synthesis of3-Aminofuran Derivatives[J]. Organic Letters,2005,7(7):1343-1345.
[79] Yadav, J. S., Reddy, B. V. S., Reddy, Y. J., Reddy, N. S. Three-component synthesis of2-aryl-4-arylthio-tetrahydro-2H-pyrans via the Prins-cyclization[J]. Tetrahedron Letters,2009,50(24):2877-2880.
[80] Yadlapalli, R. K., Chourasia, O. P., Perali, R. S. A facile one-pot synthesis of2-thioxo-dihydropyrimidines and polyfunctionalized pyran derivatives as mimics of novel calciumchannel modulators[J]. Tetrahedron Letters,2012,53(49):6725-6728.
[81] Elinson, M. N., Ilovaisky, A. I., Merkulova, V. M., Belyakov, P. A., Chizhov, A. O., Nikishin, G. I.Solvent-free cascade reaction:direct multicomponent assembling of2-amino-4H-chromene scaffoldfrom salicylaldehyde,malononitrile or cyanoacetate and nitroalkanes[J]. Tetrahedron,2010,66(23):4043-4048.
[82] Chen, Z. W., Zhu, Q., Su, W. K. A novel sulfonic acid functionalized ionic liquid catalyzedmulticomponent synthesis of10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dionederivatives in water[J]. Tetrahedron Letter,2011,52(20):2601-2604.
[83] Elinson, M. N., Ilovaisky, A. I., Dorofeev, A. S., Merkulova, V. M., Stepanov, N. O., Miloserdov, F.M., Ogibin, Y. N., Nikishin, G. I. Electrocatalytic multicomponent transformation of cyclic1,3-diketones,isatins,and malononitrile:facile and convenient way to functionalizedspirocyclic(5,6,7,8-tetrahydro-4H-chromene)-4,3’-oxindole system[J]. Tetrahedron,2007,63(42):10543-10548.
[84] Shaabani, A., Sarvary, A., Rezayan, A. H., Keshipour, S. Synthesis of fully substitutedpyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides[J]. Tetrahedron,2009,65(17):3492-3495.
[85] Penchal, R. N., Graham, J. B. Multicomponent Synthesis of6H-Dibenzo[b,d]pyran-6-ones and aTotal Synthesis of Cannabinol[J]. Organic Letters,2012,14(1):310-313.
[86] Jalani, H. B., Kaila, J. C., Baraiya, A. B., Pandya, A. N., Sudarsanam, V., Vasu, K. K. A versatileone-pot multicomponent synthesis of novel quinazolinon-2-yl-tetrasubstituted thiophenes[J].Tetrahedron Letters,2010,51(43):5686-5689.
[87] Wang, Y., Dong, D., Yang, Y., Huang, J., Ouyang, Y., Liu, Q. A facile and convenient one-potsynthesis of polysubstituted thiophenes from1,3-dicarbonyl compounds in water[J]. Tetrahedron,2007,63(12):2724–2728.
[88] Jalani, H. B., Pandya, A. N., Pandya, D. H., Sharma, J. A., Sudarsanam, V., Vasu, K. K. A concise,greener, solvent-free novel one-pot synthesis of trisubstituted thiophenes[J]. Tetrahedron Letters,2012,53(51):6927-6930.
[89] Mayer,T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. L., Mitchison, T. J. Smallmolecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen[J]. Science,1999,286(5441):971-974.
[90] Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A., O'Reilly, B.C. Dihydropyrimidine calcium channel blockers.3.3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents[J]. Journalof Medicinal Chemistry,1991,34(2):806-811.
[91] Kappe, C. O. Biologically active dihydropyrimidones of the Biginelli-type-a literature survey[J].European Journal of Medicinal Chemistry,2000,35(12),1043-1052.
[92] Xu, X. H., Yao, G. M., Li, Y. M., Lu, J. H., Lin, C. J., Wang, X., Kong, C. H.5-FluorouracilDerivatives from the Sponge Phakellia fusca[J]. Journal of Natural Products,2003,66(2):285-288.
[93] Pettit, G. R., Tang, Y. P., Zhang, Q. W., Bourne, G. T., Arm, C. A., Leet, J. E., Knight, J. C., Pettit,R. K., Chapuis, J. C., Doubek, D. L., Ward, F. J., Weber, C., Hooper, J. N. A. Isolation andStructures of Axistatins1-3from the Republic of Palau Marine Sponge Agelas axifera Hentschel[J].Journal of Natural Products,2013,76(3):420-424.
[94] Ralifo, P., Tenney, K., Valeriote, F. A., Crews, P. A Distinctive Structural Twist in theAminoimidazole Alkaloids from a Calcareous Marine Sponge:Isolation and Characterization ofLeucosolenamines A and B[J]. Journal of Natural Products,2007,70(1):33-38.
[95] Weston, H. E. Experimental chemotherapy of infection with agents of thepsittacosis-lymphogranuloma-trachoma group [J]. Annals of the New York Academy of Sciences,1962,98(1):275-286.
[96] a) Maliga, Z., Kapoor, T. M., Mitchison, T. J. Evidence that Monastrol Is an Allosteric Inhibitor ofthe Mitotic Kinesin Eg5[J]. Chemistry&Biology,2002,9(9),989-996; b) DeBonis, S., Simorre, J.P., Crevel, I., Lebeau, L., Skoufias, D. A., Blangy, A., Ebel, C., Gans, P., Cross, R., Hackney, D. D.,Wade, R. H., Kozielski, F. Interaction of the Mitotic Inhibitor Monastrol with Human KinesinEg5[J]. Biochemistry,2003,42(2):338-349.
[97] Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. O’Reilly, B. C.Dihydropyrimidine calcium channel blockers.3.3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents[J]. Journal ofMedicinal Chemistry,1991,34(2):806-811.
[98] Wang, Z. T., Xu, L. W., Xia, C. G., Wang, H. Q. Novel Biginelli-like three-componentcyclocondensation reaction: efficient synthesis of5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones[J]. Tetrahedron Letters,2004,45(42):7951-7953.
[99] Wang,Y. Y., Yu, J. P., Miao, Z. W., Chen, R. Y. Bifunctional primary amine-thiourea–TfOH(BPAT·TfOH) as a chiral phase-transfer catalyst: the asymmetric synthesis of dihydropyrimi-dines[J]. Organic&Biomolecular Chemistry,2011,9(8):3050-3054.
[100] Pasunooti, K. K., Chai, H., Jensen,C. N., Gorityala, B. K., Wang, S. M., Li, X. W. Amicrowave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones undermild conditions[J]. Tetrahedron Letters,2011,52(1):80-84.
[101] Fu, N. Y., Yuan, Y. F., Cao, Z., Wang, S. W., Wang, J. T., Peppe, C. Indium(III)bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for theBiginelli reaction[J]. Tetrahedron,2002,58(24):4801-4807.
[102] Litvic, M., Vecenaj, I., Ladisic, Z. M., Lovric, M., Vinkovic, V., Filipan-litvic, M. First applicationof hexaaquaaluminium(Ⅲ) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst inorganic synthesis: a simple and efficient protocol for the multigram scale synthesis of3,4-dihydropyrimidinones by Biginelli reaction[J]. Tetrahedron,2010,66(19):3463-3471.
[103] Srivastava, V. P., Yadav, L. S. Biginelli reaction starting directly from alcohols. TetrahedronLetters,2010,51(49):6436-6438.
[104] Zhang, H. H., Zhou, Z. Q., Yao, Z. G., Xu, F., Shen, Q. Efficient synthesis of pyrimidinonederivatives by ytterbium chloride catalyzed Biginelli-type reaction under solvent-free conditions[J].Tetrahedron,2009,50(14):1622-1624.
[105] Liang, B., Wang, X. T., Wang, J. X., Du, Z. Y. New three-component cyclocondensation reaction:microwaveassisted one-pot synthesis of5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones undersolvent-free conditions[J]. Tetrahedron,2007,63(9):1981-1986.
[106] Pourjavadia, A., Hosseinia, S. H., Soleymanb, R. Crosslinked poly(ionic liquid) as high loadeddual acidic organocatalyst[J]. Journal of Molecular Catalysis A: Chemical,2012,356:55-59.
[107] Heravi, M. M., Derikvand, F., Ranjbar, L., Bamoharram, F. F. H6P2W18O62.18H2O, a green andreusable catalyst for the three-component, one-pot synthesis of4,6-diarylpyrimidin-2(1H)-onesunder solvent-free conditions[J]. Synthetic Communications,2010,40(9):1256-1263.
[108] Mohan, S. B., Ravi Kumar, B. V. V., Dinda, S. C., Naik, D., Prabu Seenivasan, S., Kumar, V.,Rana, D. N., Brahmkshatriya, P. S. Microwave-assisted synthesis, molecular docking andantitubercular activity of1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives[J]. Bioorganic&Medicinal Chemistry Letters,2012,22(24):7539-7542.
[109] Mizar, P., Myrboh, B. Three-component synthesis of5:6and6:6fused pyrimidines usingKF–alumina as a catalyst[J]. Tetrahedron Letters,2008,49(36):5283-5285.
[110] Maryam, M. A., Alireza, M., Mohammad B., Rabah, B. Cheap and Efficient Protocol for theSynthesis of Tetrahydroquinazolinone, Dihydropyrimidinone, and Pyrimidinone Derivatives[J].Synthetic Communications,2010,40(1):8-20.
[111] Gao, L. J., Ji, H. L., Rong, L. C., Han, H. X., Shi, Y. H., Tu, S. J. An Efficient Synthesis of5,6-Dihydrobenzo[h]quinazoline Derivatives under Solvent-Free Conditions[J]. Journal ofHeterocyclic Chemistry,2010,47(2):358-362.
[112] Shen, Z. L., Xu, X. P., Ji, S. J. Br nsted Base-Catalyzed One-Pot Three-Component Biginelli-TypeReaction: An Efficient Synthesis of4,5,6-Triaryl-3,4-dihydropyrimidin-2(1H)-one and MechanisticStudy[J]. Journal of Organic Chemistry2010,75(4):1162-1167.
[113] Adib, M., Sheikhi, E., Bagheri, M., Bijanzadeh, H. R., Amanlou, M. Solvent-free andthree-component synthesis of1H,6H-6λ5-[1,2]benzoxaphospholo[2,3-b][1,2]benzoxaphosphol-1-ones[J]. Tetrahedron,2012,65(15):3237-3242.
[114] Verma, G. K., Raghuvanshi, K., Verma, R. K., Dwivedi, P., Singh, M. S. An efficient one-potsolvent-free synthesis and photophysical properties of9-aryl/alkyl-octahydroxanthene-1,8-diones[J].Tetrahedron,2011,67(20):3698-3704.
[115] Chowdhury, S., Nandi, G. C., Samai, S., Singh, M. S. Regioselective Synthesis ofTetrahydrothiochromen-5-ones via a One-Pot Three-Component Solvent-Free Domino Protocol[J].Organic Letter,2011,13(14):3762-3765.
[116] George J. P. Britovsek, Russell A. Taylor, Glenn J. Sunley, David J. Law, and Andrew J. P.White, Protonation of Platinum(II) Dialkyl Complexes Containing Ligands with ProximateH-Bonding Substituents[J]. Organometallics2006,25(8):2074-2079.
[117] Ye, B. H.; Tong, M. L.; Chen, X. M. Metal-organic molecular architectures with2,2-bipyridyl-likeand carboxylate ligands[J]. Coordination Chemistry Reviews,2005,249(5-6):545–565.
[118] Demyan E. Prokopchuk, Alan J. Lough and Robert H. Morris, From amine to ruthenaziridine toazaallyl: unusual transformation of di-(2-pyridylmethyl)amine on ruthenium[J]. Dalton Trans.,2011,40,10603-10608.
[119] Kahn, O.; Kr ber, J.; Jay, C. Spin Transition Molecular Materials for displays and datarecording[J]. Advanced Materials,1992,4(11):718-728.
[120] Abrahams, B. F.; Grannas, M. J.; Hudson, T. A.; Robson. R. A Simple Lithium(I) Salt with aMicroporous Structure and Its Gas Sorption Properties[J]. Angewandte Chemie InternationalEdition,2010,49(6):1087-1089.
[121] Hou, L.; Shi, W. J.; Wang, Y. Y.; Guo, Y.; Jin, C.; Shi. Q. Z. A rod packing microporousmetal–organic framework: unprecedented ukv topology, high sorption selectivity and affinity forCO2[J]. Chemical Communications,2011,47(19):5464-5466.
[122] Bertram H. J., Emberger R., Güntert M., Sommer H., Werkhoff P., Synthesis of new flavorconstituents[J]. Recent developments in flavor and fragrance chemistry,1993,3:241-259.
[123] Wu, C., Decker, E. R., Blok, N., Bui, H., You, T. J., Wang, J., Bourgoyne, A. R., Knowles, V.,Berens, K. L., Holland, G.W., Brock, T. A., Dixon, R. A. F. Discovery, modeling, and humanpharmacokinetics ofN-(2-Acetyl-4,6-dimethylphenyl)-3-(3,4-dimethylisoxazol-5-ylsulfamoyl)thiophene-2-carboxamide(TBC3711), a second generation, ETA selective, and orally bioavailable endothelin antagonist[J].Journal of Medicinal Chemistry,2004,47(8):1969-1986.
[124] Duan, H. Q., Takaishi, Y., Tori, M., Takaoka, S., Honda, G., Ito, M., Takeda, Y., Kodzhimatov, O.K., Kodzhimatov, K., Ashurmetov, O. Polysulfide Derivatives from Ferula foetida[J]. Journal ofNatural Products,2002,65(11):1667-1669.
[125] Gewald, K. Reaction of ɑ-oxomercaptans with nitriles[J], Angewandte Chemie,1961,73,114-116
[126] Gewald, K., Schinke, H., Boettcher, H. Heterocycles from C–H acidic nitriles VIII.2-Aminothiophenes from methylene active nitriles, carbonyl compounds, and sulfur[J]. ChemischeBerichte,1966,99(1):94-100.
[127] Puterova, Z., Andicsova, A., Vegh, D. Synthesis of pi-conjugated thiophenes starting fromsubstituted3-oxopropanenitriles via Gewald reaction[J]. Tetrahedron,2008,64(49):11262-11269.
[128] zbek, H., Veljkovic, I. S., Reissig, H. U. Gewald synthesis of aminothiophene carboxylic acidsproviding new dipeptide analogues[J]. Synlett,2008,20:3145-3148.
[129] McKibben, B. P., Cartwright, C. H., Castelhano, A. L. Practical synthesis of tetrasubstitutedthiophenes for use in compound libraries[J]. Tetrahedron Letters,1999,40(30):5471-5474.
[130] Treu, M., Karner, T., Kousek, R., Berger, H., Mayer, M., McConnell, D. B., Stadler, A.Microwave-assisted parallel synthesis of fused heterocycles in a novel parallel multimode reactor[J].Journal of Combinatorial Chemistry,2008,10(6):863-868.
[131] Lutjens, H., Zickgraf, A., Figler, H., Linden, J., Olsson, R. A., Scammells, P. J.2-Amino-3-benzoylthiophene allosteric enhancers of A(1) adenosine agonist binding: new3,4-, and5-modifications[J]. Journal of Medicinal Chemistry,2003,46(10):1870-1877.
[132] Chakrabarti, J. K., Hotten, T. M., Tupper, D. E. Preparation of2-methylthienobenzodiazepine ascentral nervous system agent[J]. U.S.1997, US5627178A19970506.
[133] Romagnoli, R., Baraldi, P. G., Pavani, M. G., Tabrizi, M. A., Preti, D., Fruttarolo, F., Piccagli, L.,Jung, M. K., Hamel, E., Borgatti, M., Gambari, R. Synthesis and biological evaluation of2-amino-3-(3’,4’,5’-trimethoxybenzoyl)-5-aryl thiophenes as a new class of potent antitubulinagents[J]. Journal of Medicinal Chemistry,2006,49(13):3906-3915.
[134] Duffy, J. L., Kirk, B. A., Konteatis, Z., Campbell, E. L., Liang, R., Brady, E. J., Candelore, M. R.,Ding, V. D. H., Jiang, G. Q., Liu, F., Qureshi, S. A., Saperstein, R., Szalkowski, D., Tong, S., Tota, L.M., Xie, D., Yang, X. D., Zafian, P., Zheng, S., Chapman, K. T., Zhang, B. B., Tata, J. R. Discoveryand investigation of a novel class of thiophene-derived antagonistsof the human glucagonreceptor[J]. Bioorganic&Medicinal Chemistry Letters,2005,15(5):1401-1405.
[135] Sauville, E. A., Arbuck, S. G., Messmann, R., Headlee, D., Bauer, K. S., Lush, A. R., Murgo, D.,Figg, W. D., Lahusen, T., Jaken, S., Jing, X. X., Roberge, M., Fuse, E., Kuwabara, T.,Senderowicz, A. M. Phase I trial of72-hour continuous infusion UCN-01in patients with refractoryneoplasms[J]. Journal of Clinical Oncology,2001,19(8):2319-2333.
[136] Dumur, F.; Gautier, N.; Gallego-Planas, N.; Sahin, Y.; Levillain, E.; Mercier, N.; Hudhomme, P.Novel Fused D-A Dyad and A-D-A Triad Incorporating Tetrathiafulvalene and p-Benzoquinone[J].Journal of Organic Chemistry,2004,69(6):2164-2177.
[137] Xiao, Y., Qian, X. H. Novel highly efficient fluoroionophores with a peri-effect and strongelectron-donating receptors: TICT-promoted PET and signaling response to transition metalcations with low background emission[J]. Tetrahedron Letters,2003,44(10):2087-2091.
[138] Liu, G. P., Zeng, L. Y., Cai, C. An efficient synthesis of dihydrothiophene ureidoformamides bydomino reactions of1,3-thiazolidinedione under catalyst-free conditions[J]. Green Chemistry,2011,13(4):998-1003.
[139] Anonymous. Efonidipine hydrochloride ethanol[J]. Drugs,1992,17(8):672.
[140] Stout, D. M., Meyers, A. I. Recent advance in the chemistry of dihydropyridine[J]. ChemicalReviews.,1982,82(2):223-243.
[141] Bossert, F., Meyer, H., Wehinger, E．4-Aryldihydropyridine, a new class of highly active calciumantagonists[J]. Angewandte Chemie,1981,93(9):755-763.
[142] Goldmann. S., Stoltefuss, J.1,4-Dihydropyridine: effect of chirality and conformation on calciumantagonist and calcium agonist[J]. Angewandte Chemie,1991,103(12):1587-1605.
[143] Chen, Y. L., Fang, K. C., Sheu, J.-Y., Hsu, S. L., Tzeng, C.-C. Synthesis and antibacterialevaluation of certain quinolone derivatives[J]. Journal of Medicinal Chemistry,2001,44(14):2374-2377.
[144] Roma, G., Braccio, M. D., Grossi, G., Chia, M.1,8-Naphthyridines IV.9-SubstitutedN,N-dialkyl-5-(alkylamino or cycloalkylamino)[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carbox-amides, new compounds with anti-aggressive and potent anti-inflammatory activities[J]. EuropeanJournal of Medicinal Chemistry,2000,35(11):1021-1035.
[145] Maguire, M. P., Sheets, K. R., McVety, K., Spada, A. P., Zilberstein, A. A new series of PDGFreceptor tyrosine kinase inhibitors:3-substituted quinoline derivatives[J]. Journal of medicinalchemistry,1994,37(14):2129-37.
[146] Kumar, A., Sharma, S., Tripathi, V. D., Maurya, R. A., Srivastava, S. P., Bhatia, G. A., Tamrakar, K.,Srivastava, A. K. Design and synthesis of2,4-disubstituted polyhydroquinolines as prospectiveantihyperglycemic and lipid modulating agents[J]. Bioorganic&Medicinal Chemistry,2010,18(11):4138-4148.
[147] Tu, S. J., Yan, S., Cao, X. D., Wu, S. S., Zhang, X. H., Hao, W. J., Han, Z. G., Shi, F. A facile andexpeditious microwave-assisted synthesis of4-aryl-2-ferrocenyl-quinoline derivatives viamulti-component reaction[J]. Journal of Organometallic Chemistry,2009,694(1):91-96.
[148] Zonouzi, A., Mirzazadeh, R., Peivandi, A., Dehdari, S., Efficient synthesis of N-substituted4-arylquinoline derivatives using ZnCl2or ZrO2[J]. Heterocycles,2012,85(6):1447-1455.
[149] Saha, M., Pal, A. K. Palladium(0) nanoparticles: an efficient catalyst for the one-pot synthesis ofpolyhydroquinolines[J]. Tetrahedron Letters,2011,52(38):4872-4877.
[150] Fan, X. S., Li, Y. Z., Zhang, X. Y. Qu, G. R. Wang, J. J., Hu, X. Y. An Efficient and GreenSynthesis of1,4-Dihydropyridine Derivatives through Multi-Component Reaction in IonicLiquid[J]. Heteroatom Chemistry,2006,17(5):382-398.
[151] Rong, L. C., Han, H. X., Jiang, H., Li, X. Y., Yao, C. S., Tu, S. J. Synthesis of2-{3-Oxo-1,3-di
[(un)substitutedphenyl]propyl}-1,2,3,4-tetrahydronaphthalen-1-ones under Solvent-Free Condition,Chinese Journal of Organic Chemistry,2008,28(4):746-749.
[152]郑虎.药物化学（第五版）[M].北京：人民卫生出版社，2003:69-72.
[153] Huiping Zhao, Bin Yan, Laura B. Peterson, and Brian S. J. Blagg,3-Arylcoumarin DerivativesManifest Anti-proliferative Activity through Hsp90Inhibition, ACS Medicinal Chemistry Letters,2012,3(4):327-31.
[154] Marina Roussaki a, Christos A. Kontogiorgis b, Dimitra Hadjipavlou-Litina b, Stylianos Hamilakisa, Anastasia Detsi, A novel synthesis of3-aryl coumarins and evaluation of their antioxidant andlipoxygenase inhibitory activity, Bioorganic&Medicinal Chemistry Letters2010,20(13):3889-3892.
[155] Natala Srinivasa Reddy, Muralidhar Reddy Mallireddigari, Stephen Cosenza, Kiranmai Gumireddy,Stanley C. Bell, E. Premkumar Reddy and M. V. Ramana Reddy, Synthesis of new coumarin3-(N-aryl) sulfonamides and their anticancer activity, Bioorganic&Medicinal Chemistry Letters2004,14(15):4093-4097.
[156] Freeman, F. Chemistry of malononitrile[J]. Chemical Reviews,1969,69(5):591-624.
[157] Bigi, F., Conforti, M. L., Maggi, R., Piccinno, A., Sartori, G. Clean synthesis in water: uncatalyzedpreparation of ylidenemalononitriles[J]. Green Chemistry,2000,2(3):101-103.
[158]. Elinson, M. N., Dorofeev, A. S., Feducovich, S. K., Gorbunov, S. V., Nasybullin, R. F.,Miloserdov, F. M., Nikishin, G. I. The implication of electrocatalysis, in MCR strategy:electrocatalytic multicomponent transformation of cyclic1,3-diketones, aldehydes andmalononitrile into substituted5,6,7,8-tetrahydro-4H-chromenes[J]. European Journal of OrganicChemistry,2006,19:4335-4339.
[159] Fotouhi, L., Heravi, M. M., Fatehi, A., Bakhtiari, K. Electrogenerated base-promoted synthesis oftetrahydrobenzo[b]pyran derivatives[J]. Tetrahedron Letters,2007,48(31):5379-5381.
[160] Jin, T.S., Xiao, J. C., Wang, S. J., Li, T. S., Song, X. R. An efficient and convenient approach tothe synthesis of benzopyrans by a three-component coupling of one-pot reaction[J]. Synlett,2003,13:2001-2005.
[161] Rong, L. C., Li, X. Y., Wang, H. Y., Shi, D. Q., Tu, S. J. An Efficient and Facile Synthesis of2-Amino-4,6-diarylbenzene-1,3-dicarbonitrile and1,2-Dihydro-2-oxo-4,6-diarylpyridine-3-car-bonitrile under Solvent-free Conditions[J]. Chemistry Letters,2006,35(11):1314-1315.
[162] Rong, L. C., Han, H. X., Jiang, H. Tu, S. J. An Efficient Synthesis of Indeno[1,2-b]pyridine andBenzo[h]quinoline Derivatives Under Solvent-Free Conditions[J]. Journal of HeterocyclicChemistry,2009,46(3),465-468.
[163] Meyers, A. I., Willemsen, J. J. An asymmetric synthesis of (+)-apogossypol hexamethyl ether[J].Tetrahedron Letters,1996,37(6):791-792.
[164] Medarde, M., Ramos, A. C., Caballero, E., Lopez, J. L. A new approach to the synthesis ofpodophyllotoxin based on epimerization reactions[J]. Tetrahedron Letters,1996,37(15):2663-2666.
[165] Katritzky, A. R., Zhang, G., Xie, L. Benzotriazole-Assisted Aromatic Ring Annulation: Efficientand General Syntheses of Polysubstituted Naphthalenes and Phenanthrenes[J]. Journal of OrganicChemistry,1997,62(3):721-725.
[166] Bentley, K. W. The Isoquinoline Alkaloids[J]. Rodd's Chemistry of Carbon Compounds,1998,4:507-587.
[167] Zhang, Q., Tu, G., Zhao, Y., Cheng, T. Novel bioactive isoquinoline alkaloids from Carduuscrispus. Tetrahedron,2002,58(34):6795–6798.
[168] Rong, L. C., Han, H. X. Jiang, H., Tu, S. J. Efficient NaOH-Catalyzed Reaction of AromaticAldehyde, Cyclic Ketones, and Malononitrile Under Solvent-Free Conditions Using a GrindingMethod, Synthetic Communications,2008,38(20):3530-3542.
[169] Rong, L. C., Han, H. X., Jiang, H., Zhuang, Q. Y., Wang, S. H., Tu, S. J. Synthesis of6-Amino-8-aryl-2-methyl-5,7,7(1H)-tricarbonitrile-2,3,8,8atetrahydroisoquinoline Derivativesunder Solvent-Free Conditions Using a Ginding Method [J]. Chinese Journal of Organic Chemistry,2009,29(6):962-965.
[2] Zhu, S. F., Xie, J. B., Zhang, Y. Z., Li, S.,Zhou, Q. L. Well-Defined Chiral SpiroIridium/Phosphine-Oxazoline Cationic Complexes for Highly Enantioselective Hydrogenation ofImines at Ambient Pressure[J]. Journal of the American Chemical Society,2006,128(39):12886-12891.
[3] Niu, R., Xiao, J., Liang, T., Li, X. W. Facile Synthesis of Azaarene-Substituted3-Hydroxy-2-oxindoles via Br nsted Acid Catalyzed sp3C-H Functionalization[J]. Organic Letter,2012,3(124):676-679.
[4] Narayan, R., Fro hlich, R., Wu rthwein, E. U. Synthesis of Pyrroles through a4π-ElectrocyclicRing-Closure Reaction of1-Azapentadienyl Cations[J]. The Journal of Organic Chemistry,2012,77(4):1868-1879.
[5] Wang, Q. F., Song, X. K., Chen, J., Yan, C. G. Pyridinium Ylide-Assisted One-Pot Two-Step TandemSynthesis of Polysubstituted Cyclopropanes[J]. Journal of Combinatorial Chemistry,2009,11(6):1007-1010.
[6] Wang, H. J., Mo, L. P., Zhang, Z. H. Cerium Ammonium Nitrate-Catalyzed Multicomponent Reactionfor Efficient Synthesis of Functionalized Tetrahydropyridines[J]. Combinatorial Science,2011,13(2):181-185.
[7] Tan, D. S., Foley, M. A., Shair, M. D., Schreiber, S. L. Stereoselective Synthesis of over Two MillionCompounds Having Structural Features Both Reminiscent of Natural Products and Compatible withMiniaturized Cell-Based Assays[J]. Journal of the American Chemical Society,1998,120(33):8565-8566.
[8] Schreiber, S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery[J]. Science,2000,287(5460):1964-1969.
[9] Short, P. Ernest Guenther Award in the Chemistry of Natural Products[J]. Chemical&EngineeringNews,2003,81(3):51-52.
[10] Lee, D., Sello, J. K., Schreiber, S. L. Pairwise Use of Complexity-Generating Reactions inDiversity-Oriented Organic Synthesis[J]. Organic letters,2000,2(5):709-712.
[11] Burke, M. D., Schreiber, S. L. A planning strategy for diversity-oriented synthesis[J]. AngewandteChemie International Edition,2004,43(1):46-58.
[12]李明，郭维斯，文利荣，左正泉.三组分―一锅煮‖合成4,5-二氢吡唑并[1,5-a]嘧啶[J].有机化学,2008,28:472-475.
[13] Strecker, A. Ueber die künstliche Bildung der Milchs ure und einen neuen, dem Glycocollhomologen K rper[J]. Liebigs Annalen der Chemie,1850,75(1):27-45.
[14] Hantzsch, A. Ueber die Synthese pyridinartiger Verbindungen aus Acetessig ther undAldehydammoniak[J]. Liebigs Annalen der Chemie,1882,215(1):1-82.
[15] Radziszewski, B. Ueber die Constitution des Lophins und verwandter Verbindungen[J]. Berichte derdeutschen chemischen Gesellschaft,1882,15(2):1493-1496.
[16] Biginelli, P. Ueber Aldehyduramide des Acetessig thers[J]. Berichte der deutschen chemischenGesellschaft,1891,24(2):1317-1319.
[17] Mannich, C., Krosche, W. Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak undAntipyrin[J]. Archiv der Pharmazie,1912,250(1):647-667.
[18] Passerini, M., Isonitriles, I. Compound of p-isonitrileazobenzene with acetone and acetic acid[J].Gazzetta Chimica Italiana,1921,51(II),126-129.
[19] Ugi, I., Mey, R., Fetzer, U., Steinbruckner, C. Versuche mit Isonitrilen[J]. Angewandte ChemieInternational Edition,1959,71:386.
[20] Divanfard, H. R., Lysenko, Z., Wang, P. C., Joullie, M. M. An International Journal for RapidCommunication of Synthetic Organic Chemistry[J]. Synthetic Communications,1978,8(4):269-273.
[21] Weber, L., Wallbaum, S., Broger, C., et al. Optimierung der bilogischen aktivitaet yonkombinatorischen verbindungsbibliotheken durch einen genetischen algorithmus[J]. AngewandteChemie International,1995,(107):2452-2454.
[22] Keating, T. A., Armstrong, R. W. Molecular Diversity via a Convertible Isocyanide in the UgiFour-Component Condensation[J]. Journal of the American Chemical Society,1995,117(29):7842-7843.
[23] a. Barry, B. T., Dennis, G. H. Natural Product Synthesis Using Multicomponent ReactionStrategies[J]. Chemical Reviews,2009,109(9):4439-4486. b. Alexander, D. Recent Developmentsin Isocyanide Based Multicomponent Reactions in Applied Chemistry[J]. Chemical Reviews,2006,106(1):17-89.
[24] Bienayme, H., Hulme, C., Oddon, G., Schmitt, P. Maximizing synthetic efficiency: Multi-componenttransformations lead the way[J]. Chemistry-A European Journal,2000,8(16):3321-3329.
[25] Hantzsch, A. Neu Bildungsweise von Pyrrolderivaten[J]. Berichte der deutschen chemischenGesellschaft,1890,23(1):1474-1476.
[26] Khalili, B., Jajarmi, P., Eftekhari-Sis, B., Hashemi, M. M. Novel One-Pot, Three-ComponentSynthesis of New2-Alkyl-5-aryl-(1H)-pyrrole-4-ol in Water[J]. The Journal of Organic Chemistry,2008,76(3):2090-2095.
[27] Sakhno, Y. I., Desenko, S. M., Shishkina, S. V.; Shishkin, O. V., Sysoyev, D. O., Groth, U., Kappe, C.O., Chebanov, V. A. Multicomponent cyclocondensation reactions of minoazoles, arylpyruvicacids and aldehydes with controlled chemoselectivity[J]. Tetrahedron,2008,64(49):11041-11049.
[28] Attanasi, Q. A., Favi, G., Mantellini, F., Moscatelli, G., Santeusanio, S. Synthesis of FunctionalizedPyrroles via Catalyst-and Solvent-Free Sequential Three-Component Enamine AzoeneAnnulation[J]. The Journal of Organic Chemistry,2011,76(8):2860-2866.
[29] Galliford, C. V., Scheidt, K. A. Catalytic Multicomponent Reactions for the Synthesis of N-ArylTrisubstituted Pyrroles[J]. The Journal of Organic Chemistry,2007,72(5):1811-1813.
[30] Frolova, L. V., Evdokimov, N. M., Hayden, K., Malik, I., Rogelj, S., Kornienko, A., Magedov, I. V.One-Pot Multicomponent Synthesis of Diversely Substituted2-Aminopyrroles. A Short GeneralSynthesis of Rigidins A, B, C, and D[J]. Organic Letters,2011,13(5):1118-1121.
[31] Safari, J., Khalili, S. D., Rezaei, M., Banitaba, S. H., Meshkani, F. Nanocrystalline magnesiumoxide: a novel and efficient catalyst for facile synthesis of2,4,5-trisubstituted imidazolederivatives[J]. Monatshefte fuer Chemie,2010,141(12):1339-1345.
[32] Bahrami, K., Khodaei, M. M., Nejati, A. One-pot synthesis of1,2,4,5-tetrasubstituted and2,4,5-trisubstituted imidazoles by zinc oxide as efficient and reusable catalyst[J]. Monatshefte fuerChemie,2011,142(2):159-162.
[33] Mamedov, V. A., Zhukova, M. A., Beschastnova, T. N., Gubaidullin, A. T., Rakov, D. V. A simpleand efficient method for the synthesis of highly substituted imidazoles using3-aroylquinoxalin-2(1H)-ones[J]. Tetrahedron Letters,2011,52(33):4280-428.
[34] Siamaki, A. R., Arndtsen, B. A. A Direct One Step Synthesis of Imidazoles from Imines and AcidChlorides: A Palladium Catalyzed Multicomponent Coupling Approach[J]. Journal of the AmericanChemical Society,2006,128(18):6050-6051.
[35] Guchhait, S. K., Chandgude, A. L., Priyadarshani, G. CuSO4Glucose for in Situ Generation ofControlled Cu(I) Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehydewith Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles[J]. The Journal ofOrganic Chemistry,2012,77(9):4438-4444.
[36] Robin, S. B., Van, V. B., Nanda, E. S., Rob, F. S., Kanter, D., Frans, J. J., Christian, V. S.,Marcel, S.,Matthias, B. F., Marinus, B. G., Romano, V. A. O. Multicomponent synthesis of2-imidazolines[J].The Journal of Organic Chemistry,2005,70(9):3542-3553.
[37] Powner, M. W., Zheng, S. L., Szostak, J. W. Multicomponent Assembly of Proposed DNAPrecursors in Water[J]. Journal of the American Chemical Society,2012,134(33):13889-13895.
[38] Alinezhad, H., Tajbakhsh, M., Zare, M. Catalyst-free one-pot synthesis of1,4,5-trisubstitutedpyrazoles in2,2,2-trifluoroethanol[J]. Journal of Fluorine Chemistry,2011,132(11):995-1000.
[39] Adib, M., Sayahi, M. H., Rahbari, S. Reactions between isocyanides and dialkylacetylenedicarboxylates in the presence of1,2-diacylhydrazines.One-pot synthesis of highlyfunctionalized pyrazoles[J]. Tetrahedron Letters,2005,46(38):6545-6547.
[40] Muravyova, E. A., Desenko, S. M., Rudenko, R. V., Shishkina, S. V., Shishkin, O. V., Sen’ko, Y. V.,Vashchenko, E. V., Chebanov, V. A. Switchable selectivity in multicomponent heterocyclizations ofacetoacetamides, aldehydes,and3-amino-1,2,4-triazoles/5-aminopyrazoles[J]. Tetrahedron,2011,41(2):9389-9400.
[41] Dandia, A., Laxkar, A. K., Singh, R. New multicomponent domino reaction on water:highlydiastereoselective synthesis of spiro[indoline-3,4’-pyrazolo[3,4-b]pyridines]catalyzed by NaCl[J].Tetrahedron Letter,2012,53(24):3012–3017.
[42] Shaabani, A., Sarvary, A., Rezayan, A. H., Keshipour, S. Synthesis of fully substitutedpyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides[J]. Tetrahedron,2009,65(17):3492-3495.
[43] Valentin, A. C., Vyacheslav, E. S., Sergey, M. D., Vitaliy, N. C., Svetlana, V. S., Oleg, V. S., Kiril,M. K., Oliver, K. C. One-Pot Multicomponent Route to Pyrazoloquinolizinones[J]. Organic Letters,2007,9(9):1691-1694.
[44] Chen, Z. Y., Wu, J. Efficient Generation of Biologically Active H-Pyrazolo[5,1-a]isoquinolines viaMulticomponent Reaction[J]. Organic Letters,2010,12(21):4856–4859.
[45] Hantzsch, A. Condensationprodukte aus Aldehydammoniak und Ketoniartigen Verbindungen[J].Chemische Berichte,1881,14:1637-1638.
[46] Xia, J. J., Wang, G. W. One-Pot Synthesis and Aromatization of1,4-Dihydropyridines in RefluxingWater[J]. Synthesis,2005,14:2379-2383.
[47] Knoevenagel, E., Fries, A. Synthesen in der Pyridinreihe. Ueber eine Erweiterung derHantzsch'schen Dihydropyridinsynthese[J]. Berichte der deutschen chemischen Gesellschaft,1898,31(1):761-767.
[48] Khan, A. T.,Lal, M.,Khan, M. M. Synthesis of highly functionalized piperidines by one-potmulticomponent reaction using tetrabutylammonium tribromide (TBATB)[J]. Tetrahedron Letter.2010,51(33):4419-4424.
[49] Liu, W. B., Jiang, H. F., Zhu, S. F., Wang, W. Hydroalkylation leading to heterocycliccompounds(Part2): practical synthesis of polysubstituted1,2,3,4-tetrahydropyridines throughmulticomponent reactions(MCRs)[J]. Tetrahedron,2009,65(38):7985-7988.
[50] Sridhar, M., Ramanaiah, B. C., Narsaiah, C., Mahesh, B., Kumaraswamy, M., Mallu, K. K. R.,Ankathi, V. M., Rao, P. S. Novel ZnCl2-catalyzed one-pot multicomponent synthesis of2-amino-3,5-dicarbonitrile-6-thio-pyridines[J]. Tetrahedron Letter.2009,50(27):3897-3900.
[51] Evdokimov, N. M., Kireev, A. S., Yakovenko, A. A., Yu. M., Magedov, A. I. V., Kornienko, A.One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reactionof Malononitrile with Aldehydes and Thiols[J]. The Journal of Organic Chemistry.2007,72(9):3443-3453.
[52] Li, M., Zuo, Z. G., Wen, L. R., Wang, S.W. Microwave-Assisted Combinatorial Synthesis ofHexa-Substituted1,4-Dihydropyridines Scaffolds Using One-Pot Two-Step MulticomponentReaction followed by a S-Alkylation[J]. Journal of Combinatorial Chemistry,2008,10(3):436-441.
[53] Abu, T. K., Tasneem, P., Lokman, H. C. Effects of Substituents in the-Position of1,3-DicarbonylCompounds in Bromodimethylsulfonium Bromide-Catalyzed Multicomponent Reactions: A FacileAccess to Functionalized Piperidines[J]. The Journal of Organic Chemistry,2008,73(21):8398-8402.
[54] Biginelli, P. Ueber Aldehyduramide des Acetessigaethers[J]. Berichte der Deutschen ChemischenGesellschaft,1891,24:1317-1319.
[55] Pourmousavi, S. A., Hasani, M. H2SO4-Silica Catalyzed One-Pot and Efficient Synthesis ofDihydropyrimidinones Under Solvent-Free Conditions[J]. E-Journal of Chemistry,2011,8(1):462-466.
[56] Lei, M., Ma, L., Hu, L. H. Cu(ClO4)2·6H2O as an efficient catalyst for the synthesis of3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions[J]. Synthetic Communications,2011,41(20):3071-3077.
[57] Madhusudana, R. B. M., Pasha, M. A. Iodine-catalyzed versatile synthesis of4,6-diarylpyrimidin-2(1H)-ones (DAPMs) via one-pot, multicomponent reaction[J]. SyntheticCommunications,2011,41(13):1875-1880.
[58]彭家建，邓友全.室温离子液体催经―一锅法‖合成3，4-二氢嘧啶-2-酮[J]，有机化学，2002，22（1）：71.
[59] Valentin, A., Chebanov, Elena, A., Muravyova, S. M., Desenko, et al. Microwave-AssistedThree-Component Synthesis7-Aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and Their Selective Reduction[J]. Journal of Combinatorial Chemistry,2006,(3):427-434.
[60] Hulme, R., Zamora, O. D. P., Mota, E. J., Pasten, M. A., Contreras-Rojas, R., Miranda, R.,Valencia-Hernandez, I., Correa-Basurto, J., Trujillo-Ferrara, J., Delgado, F. Cyanamide:a convenientbuilding block to synthesize4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via amulticomponent reaction[J]. Tetrahedron,2008,64(15):3372-3380.
[61] Shaabani, A., Seyyedhamzeh, M., Maleki, A., Hajishaabanha, F. Diketene as an alternative substratefor a new Biginelli-like multicomponent reaction: one-pot synthesis of5-carboxamide substituted3,4-dihydropyrimidine-2(1H)ones[J]. Tetrahedron,2010,66(23):4040-4042.
[62] Chebil, E., Touil, S. Behaviour of β-keto--carbethoxyphosphonates and phosphine oxides in thebiginelli multicomponent reaction: regioselective synthesis of5-carbethoxy-6-phosphono-methyl-3,4-dihydropyrimidin-2-ones[J]. Heterocycles,2012,85(11):2765-2774.
[63] Zhang, M., Jiang, H. F., Liu, H. L., Zhu, Q. H. Convenient One-Pot Synthesis of MultisubstitutedTetrahydropyrimidines via Catalyst-Free Multicomponent Reactions[J]. Organic Letters,2007,9(21):4111-4113.
[64] Kumar, R., Raghuvanshi, K., Verma, R. K., Singh, M. S. Application of cyclic-1,3-diketones indomino and multicomponent reactions: facile route to highly functionalizedchromeno[2,3-d]pyrimidinones and diazabenzo[b]fluorenones under solvent-free conditions[J].Tetrahedron Letter,2010,51(45):5933-5936.
[65] Majumder, S., Gipson, K. R., Odom, A. L. A Multicomponent Coupling Sequence for Direct Accessto Substituted Quinolines[J]. Organic Letters,2009,11(20):4720-4723.
[66] Shindoh, N., Tokuyama, H., Takemoto, Y., Takasu, K. Auto-Tandem Catalysis in the Synthesis ofSubstituted Quinolines from Aldimines and Electron-Rich Olefins: Cascade Povarov-Hydrogen-Transfer Reaction[J]. The Journal of Organic Chemistry,2008,73(19):7451-7456.
[67] Guchhait, S. K., Jadeja, K., Madaan, G. A new process of multicomponent Povarov reaction–aerobicdehydrogenation: synthesis of polysubstituted quinolines[J]. Tetrahedron Letters,2009,50(49):6861-6865.
[68] Kadutskii, A. P., Kozlov, N. G., Pashkovskii, F. S. Synthesis of benzo [f] quinoline derivatives bythree-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde[J].Russian Journal of Organic Chemistry,2009,45(3):399-403.
[69] Song, S. J., Shan, Z. X., Jin, Y. One–pot synthesis of hexahydroquinolines via Hantzschfour-component reaction catalyzed by a cheap amino alcohol[J]. Synthetic Communications,2010,40(20):3067-3077.
[70] Nezhad, A. K., Sarikhani, S., Shahidzadeh, E. S., Panahi, F. L-Proline-promoted three-componentreaction of anilines, aldehydes and barbituric acids/malononitrile: regioselective synthesis of5-arylpyrimido-[4,5-b]quinoline-diones and2-amino-4-arylquinoline-3-carbonitriles in water[J].Green Chemistry,2012,14(10):2876-2884.
[71] Ding, Q. P., Wu, J. Lewis Acid-and Organocatalyst-Cocatalyzed Multicomponent Reactions of2-Alkynylbenzaldehydes, Amines, and Ketones[J]. Organic Letters,2007,9(24):4959-4962.
[72] Gao, K., Wu, J. Synthesis of Functionalized1,2-Dihydroisoquinolines via Multicomponent One-PotReaction of2-Alkynylbenzaldehyde, Amine, Zinc, and Allylic Bromide or Benzyl Bromide[J]. TheJournal of Organic Chemistry,2007,72(9):8611-8613.
[73] Heravi, M. M., Sadjad, S., Mokhtari, H. N., Oskooie, H. A., Shoar, R. H., Bamoharram, F. F. Anovel multi-component synthesis of4-arylaminoquinazolines[J]. Tetrahedron Letters,2009,50(8):943-945.
[74] Devi, N. S., Singh, S. J., Singh, O. M. An Efficient One-Pot Multicomponent Synthesis of2,3-Dihydro-3-alkyl/aryl-2-thioxoquinazolin-4(1H)-ones under Solvent-Free Conditions[J]. Synlett,2012,23(14):2111-2115.
[75] Shang,Y. J., Ju, K., He, X. W., Hu, J. S., Yu, S.Y., Zhang, M., Liao, K. S., Wang, L. F., Zhang, P.Copper-Catalyzed Multicomponent Reaction: Synthesis of4-Arylsulfonylimino-4,5-dihydrofuranDerivatives[J]. The Journal of Organic Chemistry,2010,75(16):5743–5745.
[76] Sun, C., Ji, S. J., Liu, Y. Facile synthesis of3-(2-furanyl)indoles via a multicomponent reaction[J],Tetrahedron Letter,2007,48(51):8987-8989.
[77] Shaabani, A., Rezayan, A. H., Ghasemi, S., Sarvary, A. A mild and efficient method for the synthesisof2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylates via an isocyanide-based multicomponentreaction[J]. Tetrahedron Letter,2009,50(13):1456-1458.
[78] Ma, C., Yang, Y. W. Thiazolium-Mediated Multicomponent Reactions: A Facile Synthesis of3-Aminofuran Derivatives[J]. Organic Letters,2005,7(7):1343-1345.
[79] Yadav, J. S., Reddy, B. V. S., Reddy, Y. J., Reddy, N. S. Three-component synthesis of2-aryl-4-arylthio-tetrahydro-2H-pyrans via the Prins-cyclization[J]. Tetrahedron Letters,2009,50(24):2877-2880.
[80] Yadlapalli, R. K., Chourasia, O. P., Perali, R. S. A facile one-pot synthesis of2-thioxo-dihydropyrimidines and polyfunctionalized pyran derivatives as mimics of novel calciumchannel modulators[J]. Tetrahedron Letters,2012,53(49):6725-6728.
[81] Elinson, M. N., Ilovaisky, A. I., Merkulova, V. M., Belyakov, P. A., Chizhov, A. O., Nikishin, G. I.Solvent-free cascade reaction:direct multicomponent assembling of2-amino-4H-chromene scaffoldfrom salicylaldehyde,malononitrile or cyanoacetate and nitroalkanes[J]. Tetrahedron,2010,66(23):4043-4048.
[82] Chen, Z. W., Zhu, Q., Su, W. K. A novel sulfonic acid functionalized ionic liquid catalyzedmulticomponent synthesis of10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dionederivatives in water[J]. Tetrahedron Letter,2011,52(20):2601-2604.
[83] Elinson, M. N., Ilovaisky, A. I., Dorofeev, A. S., Merkulova, V. M., Stepanov, N. O., Miloserdov, F.M., Ogibin, Y. N., Nikishin, G. I. Electrocatalytic multicomponent transformation of cyclic1,3-diketones,isatins,and malononitrile:facile and convenient way to functionalizedspirocyclic(5,6,7,8-tetrahydro-4H-chromene)-4,3’-oxindole system[J]. Tetrahedron,2007,63(42):10543-10548.
[84] Shaabani, A., Sarvary, A., Rezayan, A. H., Keshipour, S. Synthesis of fully substitutedpyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides[J]. Tetrahedron,2009,65(17):3492-3495.
[85] Penchal, R. N., Graham, J. B. Multicomponent Synthesis of6H-Dibenzo[b,d]pyran-6-ones and aTotal Synthesis of Cannabinol[J]. Organic Letters,2012,14(1):310-313.
[86] Jalani, H. B., Kaila, J. C., Baraiya, A. B., Pandya, A. N., Sudarsanam, V., Vasu, K. K. A versatileone-pot multicomponent synthesis of novel quinazolinon-2-yl-tetrasubstituted thiophenes[J].Tetrahedron Letters,2010,51(43):5686-5689.
[87] Wang, Y., Dong, D., Yang, Y., Huang, J., Ouyang, Y., Liu, Q. A facile and convenient one-potsynthesis of polysubstituted thiophenes from1,3-dicarbonyl compounds in water[J]. Tetrahedron,2007,63(12):2724–2728.
[88] Jalani, H. B., Pandya, A. N., Pandya, D. H., Sharma, J. A., Sudarsanam, V., Vasu, K. K. A concise,greener, solvent-free novel one-pot synthesis of trisubstituted thiophenes[J]. Tetrahedron Letters,2012,53(51):6927-6930.
[89] Mayer,T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. L., Mitchison, T. J. Smallmolecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen[J]. Science,1999,286(5441):971-974.
[90] Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A., O'Reilly, B.C. Dihydropyrimidine calcium channel blockers.3.3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents[J]. Journalof Medicinal Chemistry,1991,34(2):806-811.
[91] Kappe, C. O. Biologically active dihydropyrimidones of the Biginelli-type-a literature survey[J].European Journal of Medicinal Chemistry,2000,35(12),1043-1052.
[92] Xu, X. H., Yao, G. M., Li, Y. M., Lu, J. H., Lin, C. J., Wang, X., Kong, C. H.5-FluorouracilDerivatives from the Sponge Phakellia fusca[J]. Journal of Natural Products,2003,66(2):285-288.
[93] Pettit, G. R., Tang, Y. P., Zhang, Q. W., Bourne, G. T., Arm, C. A., Leet, J. E., Knight, J. C., Pettit,R. K., Chapuis, J. C., Doubek, D. L., Ward, F. J., Weber, C., Hooper, J. N. A. Isolation andStructures of Axistatins1-3from the Republic of Palau Marine Sponge Agelas axifera Hentschel[J].Journal of Natural Products,2013,76(3):420-424.
[94] Ralifo, P., Tenney, K., Valeriote, F. A., Crews, P. A Distinctive Structural Twist in theAminoimidazole Alkaloids from a Calcareous Marine Sponge:Isolation and Characterization ofLeucosolenamines A and B[J]. Journal of Natural Products,2007,70(1):33-38.
[95] Weston, H. E. Experimental chemotherapy of infection with agents of thepsittacosis-lymphogranuloma-trachoma group [J]. Annals of the New York Academy of Sciences,1962,98(1):275-286.
[96] a) Maliga, Z., Kapoor, T. M., Mitchison, T. J. Evidence that Monastrol Is an Allosteric Inhibitor ofthe Mitotic Kinesin Eg5[J]. Chemistry&Biology,2002,9(9),989-996; b) DeBonis, S., Simorre, J.P., Crevel, I., Lebeau, L., Skoufias, D. A., Blangy, A., Ebel, C., Gans, P., Cross, R., Hackney, D. D.,Wade, R. H., Kozielski, F. Interaction of the Mitotic Inhibitor Monastrol with Human KinesinEg5[J]. Biochemistry,2003,42(2):338-349.
[97] Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. O’Reilly, B. C.Dihydropyrimidine calcium channel blockers.3.3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents[J]. Journal ofMedicinal Chemistry,1991,34(2):806-811.
[98] Wang, Z. T., Xu, L. W., Xia, C. G., Wang, H. Q. Novel Biginelli-like three-componentcyclocondensation reaction: efficient synthesis of5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones[J]. Tetrahedron Letters,2004,45(42):7951-7953.
[99] Wang,Y. Y., Yu, J. P., Miao, Z. W., Chen, R. Y. Bifunctional primary amine-thiourea–TfOH(BPAT·TfOH) as a chiral phase-transfer catalyst: the asymmetric synthesis of dihydropyrimi-dines[J]. Organic&Biomolecular Chemistry,2011,9(8):3050-3054.
[100] Pasunooti, K. K., Chai, H., Jensen,C. N., Gorityala, B. K., Wang, S. M., Li, X. W. Amicrowave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones undermild conditions[J]. Tetrahedron Letters,2011,52(1):80-84.
[101] Fu, N. Y., Yuan, Y. F., Cao, Z., Wang, S. W., Wang, J. T., Peppe, C. Indium(III)bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for theBiginelli reaction[J]. Tetrahedron,2002,58(24):4801-4807.
[102] Litvic, M., Vecenaj, I., Ladisic, Z. M., Lovric, M., Vinkovic, V., Filipan-litvic, M. First applicationof hexaaquaaluminium(Ⅲ) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst inorganic synthesis: a simple and efficient protocol for the multigram scale synthesis of3,4-dihydropyrimidinones by Biginelli reaction[J]. Tetrahedron,2010,66(19):3463-3471.
[103] Srivastava, V. P., Yadav, L. S. Biginelli reaction starting directly from alcohols. TetrahedronLetters,2010,51(49):6436-6438.
[104] Zhang, H. H., Zhou, Z. Q., Yao, Z. G., Xu, F., Shen, Q. Efficient synthesis of pyrimidinonederivatives by ytterbium chloride catalyzed Biginelli-type reaction under solvent-free conditions[J].Tetrahedron,2009,50(14):1622-1624.
[105] Liang, B., Wang, X. T., Wang, J. X., Du, Z. Y. New three-component cyclocondensation reaction:microwaveassisted one-pot synthesis of5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones undersolvent-free conditions[J]. Tetrahedron,2007,63(9):1981-1986.
[106] Pourjavadia, A., Hosseinia, S. H., Soleymanb, R. Crosslinked poly(ionic liquid) as high loadeddual acidic organocatalyst[J]. Journal of Molecular Catalysis A: Chemical,2012,356:55-59.
[107] Heravi, M. M., Derikvand, F., Ranjbar, L., Bamoharram, F. F. H6P2W18O62.18H2O, a green andreusable catalyst for the three-component, one-pot synthesis of4,6-diarylpyrimidin-2(1H)-onesunder solvent-free conditions[J]. Synthetic Communications,2010,40(9):1256-1263.
[108] Mohan, S. B., Ravi Kumar, B. V. V., Dinda, S. C., Naik, D., Prabu Seenivasan, S., Kumar, V.,Rana, D. N., Brahmkshatriya, P. S. Microwave-assisted synthesis, molecular docking andantitubercular activity of1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives[J]. Bioorganic&Medicinal Chemistry Letters,2012,22(24):7539-7542.
[109] Mizar, P., Myrboh, B. Three-component synthesis of5:6and6:6fused pyrimidines usingKF–alumina as a catalyst[J]. Tetrahedron Letters,2008,49(36):5283-5285.
[110] Maryam, M. A., Alireza, M., Mohammad B., Rabah, B. Cheap and Efficient Protocol for theSynthesis of Tetrahydroquinazolinone, Dihydropyrimidinone, and Pyrimidinone Derivatives[J].Synthetic Communications,2010,40(1):8-20.
[111] Gao, L. J., Ji, H. L., Rong, L. C., Han, H. X., Shi, Y. H., Tu, S. J. An Efficient Synthesis of5,6-Dihydrobenzo[h]quinazoline Derivatives under Solvent-Free Conditions[J]. Journal ofHeterocyclic Chemistry,2010,47(2):358-362.
[112] Shen, Z. L., Xu, X. P., Ji, S. J. Br nsted Base-Catalyzed One-Pot Three-Component Biginelli-TypeReaction: An Efficient Synthesis of4,5,6-Triaryl-3,4-dihydropyrimidin-2(1H)-one and MechanisticStudy[J]. Journal of Organic Chemistry2010,75(4):1162-1167.
[113] Adib, M., Sheikhi, E., Bagheri, M., Bijanzadeh, H. R., Amanlou, M. Solvent-free andthree-component synthesis of1H,6H-6λ5-[1,2]benzoxaphospholo[2,3-b][1,2]benzoxaphosphol-1-ones[J]. Tetrahedron,2012,65(15):3237-3242.
[114] Verma, G. K., Raghuvanshi, K., Verma, R. K., Dwivedi, P., Singh, M. S. An efficient one-potsolvent-free synthesis and photophysical properties of9-aryl/alkyl-octahydroxanthene-1,8-diones[J].Tetrahedron,2011,67(20):3698-3704.
[115] Chowdhury, S., Nandi, G. C., Samai, S., Singh, M. S. Regioselective Synthesis ofTetrahydrothiochromen-5-ones via a One-Pot Three-Component Solvent-Free Domino Protocol[J].Organic Letter,2011,13(14):3762-3765.
[116] George J. P. Britovsek, Russell A. Taylor, Glenn J. Sunley, David J. Law, and Andrew J. P.White, Protonation of Platinum(II) Dialkyl Complexes Containing Ligands with ProximateH-Bonding Substituents[J]. Organometallics2006,25(8):2074-2079.
[117] Ye, B. H.; Tong, M. L.; Chen, X. M. Metal-organic molecular architectures with2,2-bipyridyl-likeand carboxylate ligands[J]. Coordination Chemistry Reviews,2005,249(5-6):545–565.
[118] Demyan E. Prokopchuk, Alan J. Lough and Robert H. Morris, From amine to ruthenaziridine toazaallyl: unusual transformation of di-(2-pyridylmethyl)amine on ruthenium[J]. Dalton Trans.,2011,40,10603-10608.
[119] Kahn, O.; Kr ber, J.; Jay, C. Spin Transition Molecular Materials for displays and datarecording[J]. Advanced Materials,1992,4(11):718-728.
[120] Abrahams, B. F.; Grannas, M. J.; Hudson, T. A.; Robson. R. A Simple Lithium(I) Salt with aMicroporous Structure and Its Gas Sorption Properties[J]. Angewandte Chemie InternationalEdition,2010,49(6):1087-1089.
[121] Hou, L.; Shi, W. J.; Wang, Y. Y.; Guo, Y.; Jin, C.; Shi. Q. Z. A rod packing microporousmetal–organic framework: unprecedented ukv topology, high sorption selectivity and affinity forCO2[J]. Chemical Communications,2011,47(19):5464-5466.
[122] Bertram H. J., Emberger R., Güntert M., Sommer H., Werkhoff P., Synthesis of new flavorconstituents[J]. Recent developments in flavor and fragrance chemistry,1993,3:241-259.
[123] Wu, C., Decker, E. R., Blok, N., Bui, H., You, T. J., Wang, J., Bourgoyne, A. R., Knowles, V.,Berens, K. L., Holland, G.W., Brock, T. A., Dixon, R. A. F. Discovery, modeling, and humanpharmacokinetics ofN-(2-Acetyl-4,6-dimethylphenyl)-3-(3,4-dimethylisoxazol-5-ylsulfamoyl)thiophene-2-carboxamide(TBC3711), a second generation, ETA selective, and orally bioavailable endothelin antagonist[J].Journal of Medicinal Chemistry,2004,47(8):1969-1986.
[124] Duan, H. Q., Takaishi, Y., Tori, M., Takaoka, S., Honda, G., Ito, M., Takeda, Y., Kodzhimatov, O.K., Kodzhimatov, K., Ashurmetov, O. Polysulfide Derivatives from Ferula foetida[J]. Journal ofNatural Products,2002,65(11):1667-1669.
[125] Gewald, K. Reaction of ɑ-oxomercaptans with nitriles[J], Angewandte Chemie,1961,73,114-116
[126] Gewald, K., Schinke, H., Boettcher, H. Heterocycles from C–H acidic nitriles VIII.2-Aminothiophenes from methylene active nitriles, carbonyl compounds, and sulfur[J]. ChemischeBerichte,1966,99(1):94-100.
[127] Puterova, Z., Andicsova, A., Vegh, D. Synthesis of pi-conjugated thiophenes starting fromsubstituted3-oxopropanenitriles via Gewald reaction[J]. Tetrahedron,2008,64(49):11262-11269.
[128] zbek, H., Veljkovic, I. S., Reissig, H. U. Gewald synthesis of aminothiophene carboxylic acidsproviding new dipeptide analogues[J]. Synlett,2008,20:3145-3148.
[129] McKibben, B. P., Cartwright, C. H., Castelhano, A. L. Practical synthesis of tetrasubstitutedthiophenes for use in compound libraries[J]. Tetrahedron Letters,1999,40(30):5471-5474.
[130] Treu, M., Karner, T., Kousek, R., Berger, H., Mayer, M., McConnell, D. B., Stadler, A.Microwave-assisted parallel synthesis of fused heterocycles in a novel parallel multimode reactor[J].Journal of Combinatorial Chemistry,2008,10(6):863-868.
[131] Lutjens, H., Zickgraf, A., Figler, H., Linden, J., Olsson, R. A., Scammells, P. J.2-Amino-3-benzoylthiophene allosteric enhancers of A(1) adenosine agonist binding: new3,4-, and5-modifications[J]. Journal of Medicinal Chemistry,2003,46(10):1870-1877.
[132] Chakrabarti, J. K., Hotten, T. M., Tupper, D. E. Preparation of2-methylthienobenzodiazepine ascentral nervous system agent[J]. U.S.1997, US5627178A19970506.
[133] Romagnoli, R., Baraldi, P. G., Pavani, M. G., Tabrizi, M. A., Preti, D., Fruttarolo, F., Piccagli, L.,Jung, M. K., Hamel, E., Borgatti, M., Gambari, R. Synthesis and biological evaluation of2-amino-3-(3’,4’,5’-trimethoxybenzoyl)-5-aryl thiophenes as a new class of potent antitubulinagents[J]. Journal of Medicinal Chemistry,2006,49(13):3906-3915.
[134] Duffy, J. L., Kirk, B. A., Konteatis, Z., Campbell, E. L., Liang, R., Brady, E. J., Candelore, M. R.,Ding, V. D. H., Jiang, G. Q., Liu, F., Qureshi, S. A., Saperstein, R., Szalkowski, D., Tong, S., Tota, L.M., Xie, D., Yang, X. D., Zafian, P., Zheng, S., Chapman, K. T., Zhang, B. B., Tata, J. R. Discoveryand investigation of a novel class of thiophene-derived antagonistsof the human glucagonreceptor[J]. Bioorganic&Medicinal Chemistry Letters,2005,15(5):1401-1405.
[135] Sauville, E. A., Arbuck, S. G., Messmann, R., Headlee, D., Bauer, K. S., Lush, A. R., Murgo, D.,Figg, W. D., Lahusen, T., Jaken, S., Jing, X. X., Roberge, M., Fuse, E., Kuwabara, T.,Senderowicz, A. M. Phase I trial of72-hour continuous infusion UCN-01in patients with refractoryneoplasms[J]. Journal of Clinical Oncology,2001,19(8):2319-2333.
[136] Dumur, F.; Gautier, N.; Gallego-Planas, N.; Sahin, Y.; Levillain, E.; Mercier, N.; Hudhomme, P.Novel Fused D-A Dyad and A-D-A Triad Incorporating Tetrathiafulvalene and p-Benzoquinone[J].Journal of Organic Chemistry,2004,69(6):2164-2177.
[137] Xiao, Y., Qian, X. H. Novel highly efficient fluoroionophores with a peri-effect and strongelectron-donating receptors: TICT-promoted PET and signaling response to transition metalcations with low background emission[J]. Tetrahedron Letters,2003,44(10):2087-2091.
[138] Liu, G. P., Zeng, L. Y., Cai, C. An efficient synthesis of dihydrothiophene ureidoformamides bydomino reactions of1,3-thiazolidinedione under catalyst-free conditions[J]. Green Chemistry,2011,13(4):998-1003.
[139] Anonymous. Efonidipine hydrochloride ethanol[J]. Drugs,1992,17(8):672.
[140] Stout, D. M., Meyers, A. I. Recent advance in the chemistry of dihydropyridine[J]. ChemicalReviews.,1982,82(2):223-243.
[141] Bossert, F., Meyer, H., Wehinger, E．4-Aryldihydropyridine, a new class of highly active calciumantagonists[J]. Angewandte Chemie,1981,93(9):755-763.
[142] Goldmann. S., Stoltefuss, J.1,4-Dihydropyridine: effect of chirality and conformation on calciumantagonist and calcium agonist[J]. Angewandte Chemie,1991,103(12):1587-1605.
[143] Chen, Y. L., Fang, K. C., Sheu, J.-Y., Hsu, S. L., Tzeng, C.-C. Synthesis and antibacterialevaluation of certain quinolone derivatives[J]. Journal of Medicinal Chemistry,2001,44(14):2374-2377.
[144] Roma, G., Braccio, M. D., Grossi, G., Chia, M.1,8-Naphthyridines IV.9-SubstitutedN,N-dialkyl-5-(alkylamino or cycloalkylamino)[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carbox-amides, new compounds with anti-aggressive and potent anti-inflammatory activities[J]. EuropeanJournal of Medicinal Chemistry,2000,35(11):1021-1035.
[145] Maguire, M. P., Sheets, K. R., McVety, K., Spada, A. P., Zilberstein, A. A new series of PDGFreceptor tyrosine kinase inhibitors:3-substituted quinoline derivatives[J]. Journal of medicinalchemistry,1994,37(14):2129-37.
[146] Kumar, A., Sharma, S., Tripathi, V. D., Maurya, R. A., Srivastava, S. P., Bhatia, G. A., Tamrakar, K.,Srivastava, A. K. Design and synthesis of2,4-disubstituted polyhydroquinolines as prospectiveantihyperglycemic and lipid modulating agents[J]. Bioorganic&Medicinal Chemistry,2010,18(11):4138-4148.
[147] Tu, S. J., Yan, S., Cao, X. D., Wu, S. S., Zhang, X. H., Hao, W. J., Han, Z. G., Shi, F. A facile andexpeditious microwave-assisted synthesis of4-aryl-2-ferrocenyl-quinoline derivatives viamulti-component reaction[J]. Journal of Organometallic Chemistry,2009,694(1):91-96.
[148] Zonouzi, A., Mirzazadeh, R., Peivandi, A., Dehdari, S., Efficient synthesis of N-substituted4-arylquinoline derivatives using ZnCl2or ZrO2[J]. Heterocycles,2012,85(6):1447-1455.
[149] Saha, M., Pal, A. K. Palladium(0) nanoparticles: an efficient catalyst for the one-pot synthesis ofpolyhydroquinolines[J]. Tetrahedron Letters,2011,52(38):4872-4877.
[150] Fan, X. S., Li, Y. Z., Zhang, X. Y. Qu, G. R. Wang, J. J., Hu, X. Y. An Efficient and GreenSynthesis of1,4-Dihydropyridine Derivatives through Multi-Component Reaction in IonicLiquid[J]. Heteroatom Chemistry,2006,17(5):382-398.
[151] Rong, L. C., Han, H. X., Jiang, H., Li, X. Y., Yao, C. S., Tu, S. J. Synthesis of2-{3-Oxo-1,3-di
[(un)substitutedphenyl]propyl}-1,2,3,4-tetrahydronaphthalen-1-ones under Solvent-Free Condition,Chinese Journal of Organic Chemistry,2008,28(4):746-749.
[152]郑虎.药物化学（第五版）[M].北京：人民卫生出版社，2003:69-72.
[153] Huiping Zhao, Bin Yan, Laura B. Peterson, and Brian S. J. Blagg,3-Arylcoumarin DerivativesManifest Anti-proliferative Activity through Hsp90Inhibition, ACS Medicinal Chemistry Letters,2012,3(4):327-31.
[154] Marina Roussaki a, Christos A. Kontogiorgis b, Dimitra Hadjipavlou-Litina b, Stylianos Hamilakisa, Anastasia Detsi, A novel synthesis of3-aryl coumarins and evaluation of their antioxidant andlipoxygenase inhibitory activity, Bioorganic&Medicinal Chemistry Letters2010,20(13):3889-3892.
[155] Natala Srinivasa Reddy, Muralidhar Reddy Mallireddigari, Stephen Cosenza, Kiranmai Gumireddy,Stanley C. Bell, E. Premkumar Reddy and M. V. Ramana Reddy, Synthesis of new coumarin3-(N-aryl) sulfonamides and their anticancer activity, Bioorganic&Medicinal Chemistry Letters2004,14(15):4093-4097.
[156] Freeman, F. Chemistry of malononitrile[J]. Chemical Reviews,1969,69(5):591-624.
[157] Bigi, F., Conforti, M. L., Maggi, R., Piccinno, A., Sartori, G. Clean synthesis in water: uncatalyzedpreparation of ylidenemalononitriles[J]. Green Chemistry,2000,2(3):101-103.
[158]. Elinson, M. N., Dorofeev, A. S., Feducovich, S. K., Gorbunov, S. V., Nasybullin, R. F.,Miloserdov, F. M., Nikishin, G. I. The implication of electrocatalysis, in MCR strategy:electrocatalytic multicomponent transformation of cyclic1,3-diketones, aldehydes andmalononitrile into substituted5,6,7,8-tetrahydro-4H-chromenes[J]. European Journal of OrganicChemistry,2006,19:4335-4339.
[159] Fotouhi, L., Heravi, M. M., Fatehi, A., Bakhtiari, K. Electrogenerated base-promoted synthesis oftetrahydrobenzo[b]pyran derivatives[J]. Tetrahedron Letters,2007,48(31):5379-5381.
[160] Jin, T.S., Xiao, J. C., Wang, S. J., Li, T. S., Song, X. R. An efficient and convenient approach tothe synthesis of benzopyrans by a three-component coupling of one-pot reaction[J]. Synlett,2003,13:2001-2005.
[161] Rong, L. C., Li, X. Y., Wang, H. Y., Shi, D. Q., Tu, S. J. An Efficient and Facile Synthesis of2-Amino-4,6-diarylbenzene-1,3-dicarbonitrile and1,2-Dihydro-2-oxo-4,6-diarylpyridine-3-car-bonitrile under Solvent-free Conditions[J]. Chemistry Letters,2006,35(11):1314-1315.
[162] Rong, L. C., Han, H. X., Jiang, H. Tu, S. J. An Efficient Synthesis of Indeno[1,2-b]pyridine andBenzo[h]quinoline Derivatives Under Solvent-Free Conditions[J]. Journal of HeterocyclicChemistry,2009,46(3),465-468.
[163] Meyers, A. I., Willemsen, J. J. An asymmetric synthesis of (+)-apogossypol hexamethyl ether[J].Tetrahedron Letters,1996,37(6):791-792.
[164] Medarde, M., Ramos, A. C., Caballero, E., Lopez, J. L. A new approach to the synthesis ofpodophyllotoxin based on epimerization reactions[J]. Tetrahedron Letters,1996,37(15):2663-2666.
[165] Katritzky, A. R., Zhang, G., Xie, L. Benzotriazole-Assisted Aromatic Ring Annulation: Efficientand General Syntheses of Polysubstituted Naphthalenes and Phenanthrenes[J]. Journal of OrganicChemistry,1997,62(3):721-725.
[166] Bentley, K. W. The Isoquinoline Alkaloids[J]. Rodd's Chemistry of Carbon Compounds,1998,4:507-587.
[167] Zhang, Q., Tu, G., Zhao, Y., Cheng, T. Novel bioactive isoquinoline alkaloids from Carduuscrispus. Tetrahedron,2002,58(34):6795–6798.
[168] Rong, L. C., Han, H. X. Jiang, H., Tu, S. J. Efficient NaOH-Catalyzed Reaction of AromaticAldehyde, Cyclic Ketones, and Malononitrile Under Solvent-Free Conditions Using a GrindingMethod, Synthetic Communications,2008,38(20):3530-3542.
[169] Rong, L. C., Han, H. X., Jiang, H., Zhuang, Q. Y., Wang, S. H., Tu, S. J. Synthesis of6-Amino-8-aryl-2-methyl-5,7,7(1H)-tricarbonitrile-2,3,8,8atetrahydroisoquinoline Derivativesunder Solvent-Free Conditions Using a Ginding Method [J]. Chinese Journal of Organic Chemistry,2009,29(6):962-965.