摘要
嘧啶酮和1,4-二氢吡啶都是具有重要应用价值和良好生物活性的含氮杂环化合物.许多取代嘧啶酮是一种广谱高效抗病毒的药物。二氢嘧啶酮类化合物具有广泛的治疗和药理性质,作为药物中间体,它具有抗病毒、抗肿瘤、抗菌和消炎作用,还被作为钙离子通道的调节剂、降血压、类肾上腺素和神经肽Y (NPY)拮抗剂等,Batzelladine A and B是文献中首次报道的能够抑制HIV gp-120与CD4细胞结合的小分子量天然产物,为AIDS治疗开拓了新的领域。1,4-二氢吡啶类化合物与嘧啶酮结构类似,具有扩张血管、抗高血压、抗动脉粥状硬化、抗肿瘤、抗糖尿病、抗衰老等作用,是一类新型高效的钙离子拮抗剂。它们独特的结构和在医疗方面所表现出的巨大潜力使许多含吡啶环的生物碱成了很多研究小组的理想合成目标。许多研究小组在合成方法的改进和寻找具有生物活性的药物先导分子方面做了很多工作,但含有1,2,3-三唑基的二氢嘧啶酮尚未见报道。为了寻找具有生物活性的药物先导分子,提高新化合物的药理活性,我们将1,2,3-三唑基引进二氢嘧啶酮和1,4-二氢吡啶分子,得到一系列新的三唑基二氢嘧啶酮类化合物、1,4-二氢吡啶类化合物和吡啶类化合物,同时,寻找到一种高效、高催化活性的催化剂。所有新化合物均未见文献报道,其结构经元素分析、IR和1HNMR谱进行确认。
针对新疆地产柴油蜡含量较高的特点,以丙烯酸混合酯、苯乙烯、丙烯腈、马来酸混合酯四种单体为原料,采用自由基溶液聚合反应合成了柴油低温流动改进剂ASAMa。利用正交实验研究了单体配比,引发剂用量,溶剂用量及聚合温度对聚合物降凝效果的影响。共聚物用IR表征。针对独山子0#柴油进行降凝助滤测试,结果表明,添加剂量w (ASAMa) =5%时,对独山子0#柴油的纯降凝度可达10℃,冷滤点降低可达5℃。
本论文的主要工作:
1.以Sm(ClO4)3为催化剂,用1-苯基-1,2,3-三唑-4-醛与1,3-二羰基类化合物或环戊酮、脲或取代硫脲通过Biginelli反应合成3,4-二氢嘧啶-2-(1H)(硫)酮类化合物。
2.用1-苯基-1,2,3-三唑-4-醛与1,3-二羰基类化合物、NH4OAc通过Hantzsch反应合成1,4-二氢吡啶类化合物并在Sm(ClO4)3催化下将部分产物芳构化为吡啶类化合物。
3.先用丙烯酸、马来酸酐分别和高碳醇(十二醇、十四醇、十六醇、十八醇)反应得到相应的高碳酯,再与丙烯腈和苯乙烯以一定的摩尔比混合,在氮气保护下,恒温反应,得到ASAMa型聚合物,并针对独山子0#柴油作低温流动测试。
本论文的创新点:
1.寻找到一种新的适用于Biginelli反应和Hantzsch反应的催化剂;
2.以往的Biginelli反应中用的都是脲或硫脲,本文采用了取代的苯基硫脲,拓展了硫脲的范围。
Pyrimidone and dihydropyridine is important category of compounds including nitrogen which have applied values and biological activities. Many substituted pyrimidons are a broad highly active drug. Dihydropyrimidinones have broad therapeutic and pharmaceutical properties, as medical intermediate, which have antiviral, antitumour, antibacterial and anti-inflammatory activities, and have been used as potent calcium channel blockers, antihypertensive agents, adrenergic and neuropeptide Y (NPY) antagonist. Batzelladine A and B which are the first low molecular weight natural products reported in the literature to inhibit the binding of HIV gp-120 to CD4 cells, so disclosing a new field towards the development of AIDS therapy. 1,4-Dihydropyridines are analogy with Pyrimidones in the construction, which have expanding vascular, antihypertension, antiarteriosclerosis, antitumor, antimelituria and antifade activities. Many biologic alkalis including dihydropyridine have been used as perfect target of synthesis because of their specific construction and tremendous potentiality inhibited in medical field. Most of research groups have peoceeded a large quantity of studied in the method improvement of synthsis and in seek to leading molecules of drug with biological activity, but dihydropyrimidinones including 1,2,3-triazolyl were not reported. In order to find parent biological activity for new drugs, we designed and synthesized pyrimidone and dihydropyridine incorporating with bioactive 1,2,3-triazolyl in an effort to enhance their biological activity, a serise of desired triazolyl dihydropyrimidone compounds and 1,4-dihydropyridine compounds were obtained and seeked to an new catalyst of highly catalytic active. The structures of all the synthesized compounds were confirmed by analytical analysis and spectral data (IR, HNMR and MS).
A low temperature flow improver (ASAMa) was synthesis by free radical copolymerization reaction of acrylate, styrene, acrylonitrile and maleric anhydride for Xinjiang high Wax content diesel. The influencing factors such as monomer ratio, mass fraction of initiator and solvent and reaction temperature on cold filter plugging point (CFPP) depressing effects were investigated by orthogonally designed experiments. The depressant was applied for 0# diesel fuels of Dushanzi refinery, the SP (solidifying point) of the 0# diesel fuel was lowered by 10℃and the CFPP (cold filter plugging point) 5℃.
The major accomplishments of the thesis:
1. A novel series of 3,4-dihydropyrimidin-2(1H)-(thio)ones including substituted triazolyl were synthesised by a one-pot three component cyclocondensation reaction with a 1,3-dicarbonyl compound or cyclopentanone, 2-phenyl-1,2,3-triazoly-4-formaldehyde and urea or thiourea (substituted thiourea) using Samarium perchlorate [Sm(ClO4)3] as an efficient catalyst.
2. A novel series of 1,4-dihydropyridines including substituted triazolyl were synthesised by Hantzsch reaction with a 1,3-dicarbonyl compound, 2-phenyl-1,2,3-triazoly-4-formaldehyde and NH4Cl, and were partially aromatizated to pyridine using Samarium perchlorate [Sm(ClO4)3] as an efficient catalyst.
3. First, acroleic esters and maleic esters were separately synthesised with corresponding alcohol (lauryl alcohol, tridecyl alcohol, hexadecyl alcohol, octadecanoic alcohol), then mixed with styrene and acrylon in some ratio and thermostatic reation under nitrogen protection. ASAMa polymer was obtained and proceeded cold flow testing against 0# diesel fuels of Dushanzi refinery.
The major innovations of the thesis:
1. Seeked to an new catalyst of highly catalytic active in application to Biginelli reaction and Hantzsch reaction.
2. Only urea and thiourea were used in past Biginelli reaction, substituted thioureas were used in Biginelli reaction and continuated a field of thiourea.
引文
[1] Kappe, C. O. Synthesis and reactions of Biginelli compounds, 3. Unexpected formation of nitriles from reactions of 6-(dibromomethyl)-1,2,3,4-tetrahydro-2-oxo-5-pyrimidinecarbox- ylates with sodium azide[J]. Lieb. Anna. der Chem. 1990, 1990 (5), 505-507.
[2] Kappe, C. O. 100 years of the Biginelli dihydropyrimidine synthesis[J]. Terahedron. 1993, 49, 6937-6963.
[3] Kappe, C. O. Recent advances in the Biginelli dihydropyrimidine synthesis[J]. Acc.chem. Res. 2000, 33 (12 ), 879-888.
[4] (a) Kappe, C. O. Biologically active dihydropyrimidones of the Biginelli-type — a literature survey[J]. Eur. J. Med.Chem. 2000, 35, 1043-1052. (b) Kappe, C. O. The generation of dihydropyrimidine libraries utilizing Biginelli multicom- ponent chemistry[J]. QSAR Comb. Sci. 2003, 22 (6), 630-645.
[5] Hu, E. H.; Sidler, D. R.; Dolling, U.-H. Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimi- din-2(1H)-ones[J]. J. Org. Chem. 1998, 63 (10), 3454-3457
[6] Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillo- nite KSF [J]. Tetrahedron Lett. 1999, 40 (17), 3465-3468.
[7] Ma, Y.; Qian, C.; Wang, L.; Yang, M. Lanthanide triflate catalyzed Biginelli reaction. One-pot synthesis of dihydropyrimidinones under solvent-free conditions[J]. J. Org. Chem. 2000, 65 (12), 3864-3868.
[8] Lu, J.; Bai, Y. J.; Wang, Z. J.; Yang, B. Q.; Ma, H. R. One-pot synthesis of 3,4-dihydropyri- midin-2(1H)-ones using lanthanum chloride as a catalyst[J]. Tetrahedron Lett. 2000, 41 (47), 9075-9078 .
[9] Ranu, B. C.; Hajra, A.; Jana, U. Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the biginelli reaction[J]. J. Org. Chem. 2000, 65 (19), 6270-6272.
[10] 路军, 马怀让, 李万华. 三氯化铁催化的一锅法合成 3,4-二氢嘧啶-2-酮[J]. 有机化学. 2000, 20 (05), 815-818.
[11] 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 the Biginelli reaction[J]. Tetrahedron. 2002, 58 (24), 4801-4807.
[12] Kumar, K. A.; Kasthuraiah,M.; Reddy, C. S.; Reddy, C. D. Mn(OAc)3·2H2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones[J]. Tetrahedron Lett. 2001, 42 (44), 7873-7875.
[13] Reddy, Ch. V.; Mahesh, M.; Raju, P. V. K.; Babu, T. R.; Reddy, V. V. N. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones[J] , Tetrahedron Lett. 2002, 43 (14), 2657-2659.
[14] Lu, J.; Bai, Y. J.; Guo, Y. H.; Wang, Z. J.; Ma, H. R. CoCl2·6H2O or LaCl3·7H2O catalyzed Biginelli reaction. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones[J]. Chinese J.Chem. 2002, 22 (07), 788-790.
[15] Fan, X.; Zhang, X.; Zhang, Y. Samarium chloride catalyzed Biginelli reaction: one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones[J]. J. Chem. Res. Synop. 2002, 9, 436-438.
[16] 房芳,蒋虹,李团结,朱松磊,章晓镜.磷酸二氢钾催化下合成3 ,4-二氢嘧啶-2 (1H)-酮[J]. 徐州师范大学学报(自然科学版). 2003, 21 (2), 75-78.
[17] Shaabani, A.; Bazgir, A.; Teimouri, F. Ammonium chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions[J]. Tetrahedron Lett. 2003, 44 (4), 857-859.
[18] Maiti, G.; Kundu, P.; Guin, C. One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: an improved procedure for the Biginelli reaction[J]. Tetrahedron Lett. 2003, 44 (13), 2757-2758.
[19] Tu, S. J.; Fang, F.; Miao, C.; Jiang, H.; Feng, Y. J.; Shi, D. Q.; Wang, X. S. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst[J]. Tetrahedron Lett. 2003, 44 (32), 6153-6155.
[20] Sabitha, G.; Kiran Kumar Reddy, G. S.; Bhaskar Reddy, K.; Yadav, J. S. Vanadium(III) chloride catalyzed Biginelli condensation: solution phase library generation of dihydropyrimidin-(2H)-ones[J]. Tetrahedron Lett. 2003, 44 (34), 6497-6499.
[21] Varala, R.; Alam, M. M.; Adapa, S. A. Bismuth triflate catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones: an improved protocol for the Biginelli reaction[J]. Synlett. 2003, 1, 67-70.
[22] Ghosh, R.; Maiti, S.; Chakraborty, A. In(OTf)3-catalysed one-pot synthesis of 3,4-dihydro- pyrimidin-2(lH)-ones[J]. J. Mol. Catal. A: Chem. 2004, 217 (1-2), 47-50.
[23] Li, J. T.; Han, J. F.; Yang, J. H.; Li, T. S.; Adharvana Chari, M.; Syamasundar, K. An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation[J]. Ultr. Sono. 2003, 10 (3), 119-122.
[24] Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T. y.; Zubaidha, P. K. An efficient, high yield protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine[J]. Tetrahedron Lett. 2004, 45 (49), 9111-9113.
[25] Bose, D. S.; Fatima, L.; Mereyala, H. B.; Palaniappan, S.; John, A. Green chemistryapproaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4- dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction: comparison of ethanol, water, and solvent-free conditions[J]. J. Org. Chem. 2003, 68 (2), 587-590.
[26] Shanmugam, P.; Pernmal, P. T. 3,4-Dihydropyrimidin-2(1H)-ones via the Biginelli conden- sation promoted by triphenylphosphonium perchlorate[J]. J. Chem. Res. 2003, 9, 601-602.
[27] Tu, S.; Fang, F.; Zhu, S.; Li, T.; Zhang, X.; Zhuang, Q. A new Biginelli reaction procedure using potassium hydrogen sulfate as the promoter for an efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one.[J]. Synlett. 2004, 3, 537-539.
[28] Gangadasu, B.; Palanlappan, S.; Rao, V. J. One-pot synthesis of dihydropyrimidinones using polyaniline—bismoclite complex: a facile and reusable catalyst for the Biginelli reaction[J]. Synlett. 2004, 7, 1285-1287.
[29] Jenner, G. Effect of high pressure on Biginelli reactions: steric hindrance and mechanistic considerations[J]. Tetrahedron Lett. 2004, 45 (32), 6195-6198.
[30] Yada, J. S.; Reddy, B. V. S.; Sridhar, P.; Reddy, J. S. S.; Nagaiah, K.; Lingaiah, N.; Saiprasad, P. S. Green protocol for the Biginelli three-component reaction: Ag3PW12O40 as a novel, water-tolerant heteropolyacid for the synthesis of 3,4-dihydropyrimidinones[J]. Eur. J. Org. Chem. 2004, 3, 552-557.
[31] Bose, A. K.; Pednekar, S.; Ganguly, S. N.;Chakraborty, G.; Manhas, M. S. A simplified green chemistry approach to the Biginelli reaction using "grindstone chemistry"[J]. Tetrahedron Lett. 2004, 45(45), 8351-8353.
[32] Reddy, Y. T.; Rajitha, B.; Reddy, P. N.; Kumar, B. S.; Rao, V. P. Bismuth subnitrate catalyzed efficient synthesis of 3,4-dihydropyrimidin--2(1H)-ones: an improved protocol for the Biginelli reaction[J]. Synth. Commun. 2004, 34 (20), 3821-3825.
[33] Manjula, A.; Rao, B. V.; Neelakantan, P. An inexpensive protocol for Biginelli reaction[J]. Synth. Commun. 2004, 34 (14), 2665-2671.
[34] Han, X.; Xu, F.; Luo, Y.; Shen, Q. An efficient one-pot synthesis of dihydropyrimidinones by a samarium diiodide catalyzed Biginelli reaction under solvent-free conditions[J]. Eur. J. Org. Chem. 2005, 8, 1500-1503.
[35] Cepanec, I.; Litvi?, M.; Bartolin?i?, A.; Lovri?, M. Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction[J]. Tetrahe- Dron. 2005, 61 (17), 4275-4280.
[36] Su, W. K.; Li, J. J.; Zheng, Z.G.; Shen, Y. C. One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions[J]. Tetrahedron Lett. 2005, 46 (36), 6037-6040.
[37] Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin-2 (1H)-one using 12-tungstophosphoric acid[J]. J. Mol. Catal. A: Chem. 2005, 242 (1-2), 173-175.
[38] Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. One-pot synthesis of dihydropy-rimidinones using iodotrimethylsilane: facile and new improved protocol for the Biginelli reaction at room temperature[J]. Synlett. 2003, 6, 858-860.
[39] Wang, X.; Quan, Z.; Wang, F.; Wang, M.; Zhang, Z.; Li, Z. PEG-SO3H as catalyst for 3,4-dihydropyrimidones via Biginelli reaction under microwave and solvent-free conditions[J]. Synth. Commun. 2006, 36 (4-6), 451-456.
[40] Pasha, M. A.; Swama, N. R.; Jayashankara, V. P. One-pot synthesis of 3,4-dihydropyrimid- in-2(1H)-ones/-thiones catalyzed by zinc chloride: an improved procedure for the Biginelli reaction using microwaves under solvent-free condition[J]. Indian J. Chem., Sect. B: Org. Chem. 2005, 44 (4), 823-826.
[41] Jain, S. L.; Sharam, V. B.; Sain, B. J. Ruthenium-catalyzed Biginelli condensation: a simple and efficient one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones under mild reaction conditions[J]. Heterocycl. Chem. 2006, 43 (3), 777-779.
[42] Debache, A.; Boumoud, B.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Phenyl- boronic Acid as a Mild and Efficient Catalyst for Biginelli Reaction[J]. Tetrahedron Lett. 2006, 47 (32), 5697-5699.
[43] Suzuki, I.; Suzumura, Y.; Takeda, K. Metal triflimide as a Lewis acid catalyst for Biginelli reactions in water[J]. Tetrahedron Lett. 2006, 47 (45), 7861-7864.
[44] Wang, M.; Jiang, H.; Wang, Z. Biginelli condensation of aliphatic aldehydes catalyzed by zinc methane-sulfonate[J]. J. Chem. Res. 2005, 11, 691-693.
[45] Wang, Z. T.; Wang, S. C.; Xu, L. W. Polymer-supported ionic-liquid-catalyzed synthesis of 1,2,3,4-tetrahydro-2-oxopyrimidine-5-carboxylates via Biginelli reaction[J]. Helvetica Chimica Acta. 2005, 88 (5), 986-989.
[46] Salehi, H.; Guo, Q. X. Efficient magnesium bromide-catalyzed one-pot synthesis of sub- stituted 1,2,3,4-tetrahydropyrimidin-2-ones under solvent-free conditions[J]. Chinese J. Chem. 2005, 23, 91-97.
[47] Zhang, M.; Li, Y. Q.; Zhou, M. Y. Rapid Synthesis of 1,2,3,4-Tetrahydropyrimidin-2-ones Using Zn(NH2SO3)2 as a Catalyst under Microwave Irradiation[J]. Chinese J. Chem. 2006, 24, 282-284.
[48] Joseph, J. K.; Jain, S. L.; Sain, B. Ion exchange resins as recyclable and heterogeneous solid acid catalysts for the Biginelli condensation: an improved protocol for the synthesis of 3,4-dihydropyrimidin-2-ones[J]. J. Mol. Catal. A: Chem. 2006, 247 (1-2), 99-102.
[49] Rafiee, E.; Jafari, H. A practical and green approach towards synthesis of dihydropyrimidi- nones: using heteropoly acids as efficient catalysts[J]. Bioorganic & Med. Chem. Lett. 2006, 16 (9), 2463-2466.
[50] Liu, C. J.; Wang, J. D.; Li, Y. P. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-(thio)- ones using strontium(II) nitrate as a catalyst[J]. J. Mol. Cata. A: Chem. 2006, 258 (1-2), 367-370.
[51] Amini, M. M.; Shaabani, A.; Bazgir, A. Tangstophosphoric acid (H3PW12O40): An efficientand eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1H)-ones[J]. Catal. Commun. 2006, 7 (11), 843-847.
[52] Shanmugam, P.; Perumal, P. T. An unusual oxidation–dealkylation of 3,4-dihydropyrimidin- 2(1H)-ones mediated by Co(NO3)2·6H2O/K2S2O8 in aqueous acetonitrile[J]. Tetrahedron. 2007, 63 (3), 666-672.
[53] Bigdeli, M. A.; Jafari, S.; Mahdavinia, G. H.; Hazarkhani, H. Trichloroisocyanuric acid, a new and efficient catalyst for the synthesis of dihydropyrimidinones[J]. Catal. Commun.(In Press, Corrected Proof), Available online 25 January 2007.
[54] Nandurkar, N. S.; Bhanushali, M. J.; Bhor, M. D.; Bhanage, B. M. Y(NO3)3·6H2O: A novel and reusable catalyst for one pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions[J]. J. Mol. Catal. A: Chem. In Press, Corrected Proof, Available online 22 February 2007.
[55] Jain, S. L.; Joseph, J. K.; Singhal, S.; Sain, B. Metallophthalocyanines (MPcs) as efficient heterogeneous catalysts for Biginelli condensation: Application and comparison in catalytic activity of different MPcs for one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones[J]. J. Mol. Catal. A: Chem. 2007, 268 (1-2), 134-138.
[56] Lee, K.-Y.; Ko, K.-Y. Envirocat EPZ10: a recyclable solid acid catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones[J]. Bull. Korean Chem. Soc. 2004, 25 (12), 1929-1931.
[57] Martínez, S.; Meseguer, M.; Casas, L.; Rodríguez, E.; Molins, E.; Moreno-Ma?as, M.; Roig, A.; Sebastián, R. M.; Vallribera, A .Silica aerogel-iron oxide nanocomposites: recoverable catalysts in conjugate additions and in the Biginelli reaction[J]. Tetrahedron. 2003, 59 (9), 1553-1556.
[58] Salehi, P.; Dabiri, M.; Zolfigol, Fard, M. A.; M. A. B. Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J]. Tetrahedron Lett. 2003, 44 (14), 2889-2891.
[59] Paraskar, A. S.; Dewkar, G. K.; Sudalai, A. Cu(OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones[J]. Tetrahedron Lett. 2003, 44 (16), 3305- 3308.
[60] Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. KAl(SO4)2·12H2O supported on silica gel as a novel heterogeneous system catalyzed biginelli reaction: one-pot synthesis of dihydropyrimidinones under solvent-free conditions[J]. Appl. Catal. A: Gen. 2006, 300 (1), 85-88.
[61] Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F. 12-Molybdophosphoric acid: a recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones[J]. Catal. Commun. 2006, 7 (6), 373-376.
[62]] Zhang, X. L.; Li, Y. P.; Liu, C. J.; Wang, J. D. An efficient synthesis of 4-substituted pyrazolyl-3,4-dihydropyrimidin-2(1H)-(thio)ones catalyzed by Mg(ClO4)2 underultrasound irradiation[J]. J. Mol. Catal. A: Chem. 2006, 253 (1-2), 207-211.
[63] Vanderhoff, J. W. Carry out chemical reaction using microwave energy[P]. US 3432413, 1969-03-11.
[64] Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. The use of microwave ovens for rapid organic synthesis[J]. Tetrahedron Lett. 1986, 27 (3), 279-282..
[65] Dandia, A.; Saha, M.; Taneja, H. Synthesis of fluorinated ethyl 4-aryl-6-methyl-1,2,3,4-tetr- ahydropyrimidin-2-one/thione-5-carboxylates under microwave irradiation[J]. J. Fluo. Chem. 1998, 90 (1), 17-21.
[66] Xia, M.; Wang, Y. G. Soluble polymer-supported synthesis of Biginelli compounds[J]. Tetr- ahedron Lett. 2002, 43 (43), 7703-7705.
[67] Eynde, J. J. V.; Hecq, N.; Kataeva, O.; Kappe, C. O. Microwave-mediated regioselective synthesis of novel pyrimido[1,2-a]pyrimidines under solvent-free conditions[J]. Tetrahe- dron. 2001, 57 (9), 1785-1791.
[68] Choudhary, V. R.; Tillu, V. H.; Narkhede, V. S.; Borate, H. B.; Wakharkar, R. D. Microwave assisted solvent-free synthesis of dihydropyrimidinones by Biginelli reaction over Si-MCM-41 supported FeCl3 catalyst[J]. Catal. Commun. 2003, 4 (9), 449-453.
[69] Shaabani, A.; Bazgir, A. Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions[J]. Tetrahedron Lett. 2004, 45 (12), 2575-2577.
[70] (a) 戴冲之, 郭成, 王建强. NH4Cl 催化微波照射合成 3 ,4 -二氢嘧啶- 2-酮衍生物[J]. 化工时刊. 2004, 18 ( 6), 38-40. (b) Manhas, M. S.; Ganguly, S. N.; Mukherjee, S.; Jain, A. K.; Bose, A. K.Microwave initiated reactions: pechmann coumarin synthesis, Biginelli reaction, and acylation[J]. Tetrahedron Lett. 2006, 47 (14), 2423-2425. (c) 梁兵, 王锡天, 王进贤. 微波辐射下浓硫酸催化嘧啶酮的无溶剂合成[J]. 化学研究与应用. 2006, 18 (8), 927-930. (d) Liang, B.; Wang, X. T.; Wang, J. X.; Du, Z. Y. New three-component cyclocondensation reaction: microwave-assisted one-pot synthesis of 5-unsubstituted-3,4-dihydropyrim- idin-2(1H)-ones under solvent-free conditions[J]. Tetrahedron. 2007, 63(9), 1981- 1986.
[71] 栗兆海,陈馥衡,谢求元. 超声波在有机合成中的应用[J ] . 化学进展. 1998, 10 (1), 63-73.
[72] 李记太, 臧洪俊. 超声波应用于有机合成方面的新进展[J ]. 河北大学学报. 2000, 03 (1), 96-102.
[73] 王娜, 李保庆. 超声催化反应的研究现状和发展趋势[J ]. 化学通报. 1999, 5, 26-32.
[74] Stefani, H. A.; Oliveira, C. B.; Almeida, R. B.; Pereira, C. M. P.; Braga, R. C.; Cella, R.; Borges, V. C.; Savegnago, L.; Nogueira, C. W. Dihydropyrimidin-(2H)-ones obtained by ultrasound irradiation: a new class of potential antioxidant agents[J]. Eur. J. Med.Chem. 2006, 41 (4), 513-518.
[75] (a) Arshady, R.; Atherton, E.; Glive, D. J.; Sheepard, R. C. Peptode Synthesis. Partl. Preparation and use of polar suppprts based on poly[J]. J . Chem. Soc. 1981, 1, 529 -537. (b) Atherton, E.; Longan, C. J.; Sheppard. R. C. Peptide synthesis. Parts. Procedures for solidphase synthesis using fluorenylenthoxycarbonylamino - acid on ployamide supports. Synthesis of substance and acyl carrier protein 65-74 decapeptide[J]. J . Chem. 1981, 1, 538-546.
[76] Wipf, P.; Cunningham, A. A solid phase protocol of the biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry[J]. Tetrahedron Lett. 1995, 36 (43), 7819- 7822.
[77] Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. Fluorous synthesis: fluorous protocols for the ugi and Biginelli multicomponent condensations[J]. J. Org. Chem. 1997, 62 (9), 2917-2924.
[78] Robinett, L. D.; Yager, K. M.; Phelan, J. C. Solid-phase synthesis of dihydropyrimidine combinatorial libraries by the atwal modification of the Biginelli reaction. Abstracts of Papers, 211th national Meeting of the American Chemical Society, New Orleans, LA, 1996, American Chemical Society: Washington, DC, 1996, ORGN 122.
[79] (a) Dondoni, A.; Massi, A. Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction[J]. Tetrahedron Lett. 2001, 42 (45), 7975-7978. (b) Reddy, K. R.; Reddy, Ch. V.; Mahesh, M.; Raju, P. V. K.; Reddy, V. V. N. New environmentally friendly solvent free synthesis of dihydropyrimidinones catalysed by N-butyl-N,N-dimethyl-α-phenylethylammonium bromide[J]. Tetrahedron Lett. 2003, 44 (44), 8173-8175. (c) Yarapathi, R. V.; Kurva, S.; Tammishetti, S. Synthesis of 3,4-dihydropyrimidin-2(1H)- ones using reusable poly(4-vinylpyridine co-divinylbenzene)–Cu(II)complex Catal. Commun. 2004, 5 (9), 511-513. (d) Chari, M. A.; Syamasundar, K. Silicagel supported sodium hydrogensulfate as a heter- ogenous catalyst for high yield synthesis of 3,4-dihydropyrimidin-2 (1H)-ones[J]. J. Mol. Cata. A: Chem. 2004, 221 (1-2), 137-139.
[80] (a) Welton, T. Solvent for synthesis and catalysis[J] . Chem. Rev. 1999, 99 (8), 2071-2083. (b) Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Chemical and biochemical transformations in ionic liquids[J]. Tetrahedron. 2005, 61 (5), 1015-1060.
[81] (a) Peng, J. J.; Deng, Y. Q. Ionic liquids catalyzed Biginelli reaction under solvent-free conditions[J]. Tetrahedron Lett. 2001, 42 (34), 5917-5919. (b) Peng, J. J.; Deng, Y. Q. Catalyzed one-pot synthesis of 3 ,4-dihydropyrimidin-2(1H)- ones[J] . Chin. J . Org. Chem. 2002, 22 (1), 71-73.
[82] Kapper, C. O. The generation of dihydropyrimidine libraries utilizing Biginelli multicom-ponent chemistry[J]. QSAR Comb. Sci. 2003, 22, 630-645.
[83] Hassani, Z.; Islami, M. R.; Kalantari, M. An efficient one-pot synthesis of octahydroquina- zolinone derivatives using catalytic amount of H2SO4 in water[J]. Bio. Med. Chem. Lett. 2006, 16, 4479-4482.
[84] Ghorab, M.M.; Abdel-Gawad, S.M.; El-Gaby, M.S.A. Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents[J]. Il Farmaco. 2000, 55, 249–255.
[85] Wang, Z. T.; Xu, L. W.; Xia, C. G.; Wang, H. Q. Novel Biginelli-like three-component cyclocondensation reaction: efficient synthesis of 5-unsubstituted 3,4-dihydropyrimidin- 2(1H)-ones[J]. Tetrahedron Lett. 2004, 45, 7951-7953.
[86] Abelman, M. M.; Smith, S. C.; James, D. R. Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses[J]. Tetrahedron Lett. 2003, 44, 4559-4562.
[87] Shaabani, A.; Bazgir, A. Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions[J]. Tetrahedron Lett. 2004, 45, 2575-2577.
[88] Zhu, Y. L.; Huang, S. L.; Pan, Y. J. Highly chemoselective multicomponent Biginelli-type condensations of cycloalkanones, urea or thiourea and aldehydes[J]. Eur. J. Org. Chem. 2005, 2005 (11), 2354-2367.
[89] 朱育林. 三甲基氯硅烷参与的多组分Biginelli反应及钯催化下的Aldol缩合反应[D]. 2005.
[90] Kappe, C. O. A Reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate[J]. J. Org. Chem. 1997, 62 (21), 7201-7204.
[91] (a) 路军, 王飞利, 白银娟, 李万华. NiCl2·6H2O 催化的 Biginelli 反应——一锅法合成3,4-二氢嘧啶-2-酮[J]. 有机化学. 2002, 22 (10), 788-790. (b) 杨玲, 郭延红, 路军, 白银娟. CoCl2·6H2O 催化合成 3,4-二氢嘧啶-2-酮衍生物[J]. 化学研究与应用. 2002, 14 (6), 710-711. (c) 傅南雁, 袁耀锋, 庞美丽. 王积涛利用三溴化铟催化的 Biginelli 反应原位合成 3,4-二氢嘧啶-2-酮[J]. 高等学校化学学报. 2003, 24 (1), 79-81. (d) 彭家建, 邓友全. 室温离子液体催化“一锅法”合成 3,4-二氢嘧啶-2-酮[J]. 有机化学. 2002, 22 (1), 71-73. (e) 张素玲, 靳通收. 5-甲氧羰基-4-(4-甲氧苯基)-6-甲基-3,4-二氢嘧啶-2-酮的合成, 化学试剂. 2003, 24 (1), 43-44.
[92] Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; Brosse, C. D.; Mai, S.; Truneh, A.; Carte, B. et al. Novel alkaloids from the sponge batzella sp.: inhibitors of HIV gp120-Human CD4 binding[J]. J. Org. Chem. 1995, 60 (5),1182-1188.
[93] (a) Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. Enantioselective total synthesis of (-)-ptilomycalin A[J]. J. Am. Chem. Soc. 1995, 117 (9), 2657-2658.(b) Franklin, A. S.; Ly, S. K.; Mackin, G. H.; Overman, L. E.; Shaka, A. J. Application of the tethered Biginelli reaction for enantioselective synthesis of batzelladine alkaloids. Absolute configuration of the tricyclic guanidine portion of batzelladine B[J]. J. Org. Chem. 1999, 64 (5), 1512-1519.
[94] (a) Cohen, F.; Overman, L. E.; Ly Sakata, S. K. Asymmetric total synthesis of batzelladine D[J]. Org. Lett. 1999, 1 (13), 2169-2172. (b) Coffey, D. S.; McDonald, A. I.; Overman, L. E.; Stappenbeck, F. Enantioselective total synthesis of 13,14,15-isocrambescidin 800[J]. J. Am. Chem. Soc. 1999, 121 (29), 6944-6945. (c) Coffey, D. S.; Overman, L. E.; Stappenbeck, F. Enantioselective total syntheses of 13,14,15-isocrambescidin 800 and 13,14,15-isocrambescidin 657[J]. J. Am. Chem. Soc. 2000, 122 (20), 4904-4914. (d) Coffey, D. S.; McDonald, A. I.; Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. A practical entry to the crambescidin family of guanidine alkaloids. Enantioselective total syntheses of ptilomycalin A, crambescidin 657 and its methyl ester (Neofolitispates 2), and crambescidin 800[J]. J. Am. Chem. Soc. 2000, 122 (20), 4893-4903.
[95] Hart, H. Suggestions to authors for chemical reviews[J]. Chem. Rev. 1971, 71(1), 1-3.
[96] (a) Yasui, S.; Ohno, A. Model studies with nicotinamide derivatives[J]. Bio. Chem. 1986, 14 (1), 70-96. (b) Meijer, L. H. P.; Pandit, U. K. NAD(P)H models 20: chemoselective metal ion catalyzed reduction of α-keto-β,γ-unsaturated esters by 1,4-dihydropyridine derivatives[J]. Tetrahedron. 1985, 41 (2), 467-472.
[97] 赵炳筠, 朱晓晴, 何家淇, 夏炽中, 陈津培. 1, 4-二氢Hantzsch吡啶衍生物的合成及其1H NMR和荧光光谱研究[ J ]. 高等学校化学学报. 1999, 20 (11), 1733-1737.
[98] 房兴堂,沈露露,孙建梅. 二氢吡啶的研究进展及应用前景[J]. 饲料添加剂. 2002, 23 (7), 14-16.
[99] 史达清,牟杰,庄启亚,王香善,屠树江. 水溶液中4-芳基-1, 4-二氢吡啶衍生物的一步合成法[J]. 有机化.,2004, 24 (9), 1042-1044.
[100] (a) 王书勤主编. 世界有机药物专利制备方法大全[M].北京: 科学技术文献出版社,1996. (b) 陈芬儿主编. 有机药物合成法[M ]. 北京: 中国医药科技出版社, 1999. (c) 汪一帆主编. 世界最新药物手册[M ]. 北京: 中国医药科技出版社, 1985.
[101] Kutsuma, T.; Ikawa, H.; Sato, Y. 1, 4-dihydropyridine derivatives and pharmaceutical compositions comprising them [P ]. EP 161 877, 1985, 11 (21).
[102] 陈芬儿,余红霞,万江陵,张珩,冯秀梅,别立亮. 1,4-二氢吡啶类钙拮抗剂的合成法研究-非洛地平的合成[J]. 化学研究与应用. 1995, 7 (2), 154-157.
[103] Singh, B. N.; Collett, J. T.; Chew, C. Y. C. New perspectives in the pharmacologic therapy of cardiac arrhythmias[J]. Prog Cardiovasc Dis. 1980, 22, 243 - 301.
[104] 吴苏敏,宋明,华峰,华维一.尼莫地平的合成工艺改进[J],中国药科大学报.1998, 29 (3), 232-233.
[105] 胡艾希,伍小云,姚志钢.1, 4-二氢-2, 6-二甲基-4-(3-硝基苯基)-3, 5-吡啶二羧酸二(2-甲氧基乙基) 酯的合成[J].合成化学. 2002, 10, 345-347.
[106] 伍小云,胡艾希,谭英.钙拮抗剂普拉地平合成的改进[J]. 应用化学,2003, 20 (10), 1015-1017.
[107] (a) Cottedll I, I. C.; Usyatinsky, A. Ya.; Arnold , J. M.; Clark, D. S.; Dordick, J. S.; Michels I, P. C.; Khmelnitsky, Y. L. Microwave assisted combinatorial chemistry synthesis of substituted pyridines[J]. Tetrahedron Lett. 1998, 39, 1117-1120. (b) 包志明,刘晓钰,付强,高侠.尼群地平的微波合成[J]. 徐州师范大学学报(自然科学版). 2000, 18 (4), 48-49. (c) 屠树江,高原,于晨侠,史达清.应用微波辐射技术一步合成4-芳基-1 ,4-二氢吡啶衍生物[J]. 有机化学.2002, 22 (4), 269-271.
[108] Boecker, R. H.; Guengerich, F. P. Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-di- methyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450[J]. J. Med. Chem. 1986, 29 (9), 1596-1603.
[109] Itoh, T.; Nagata, K.; Okada, M.; Ohsawa, A. The aromatization of Hantzsch dihydropyri- dines with nitric oxide (NO)[J]. Tetrahedron Lett. 1995, 36 (13), 2269-2272.
[110] Eynde, J. J. V.; Delfosse, F.; Mayence, A.; Haverbeke, Y. V. Old reagents, new results: aromatization of Hantzsch 1,4-dihydropyridines with manganese dioxide and 2,3-dichloro- 5,6-dicyano-1,4-benzoquinone[J]. Tetrahedron. 1995, 51 (23), 6511-6516.
[111] Mashraqui, S. H.; Kamik, M. A. Catalytic oxidation of Hantzsch 1,4-dihydropyridines by RuCl3 under oxygen atmosphere[J]. Tetrahedron Lett. 1998, 39 (27), 4895-4898.
[112] 路军, 白银娟, 杨秉勤, 马怀让. 1,4-二氢吡啶衍生物合成方法的改经和芳构化研究[J]. 有机化学. 2000, 20 (4), 514-517.
[113] Varma, R. S.; Kumar, D. Mashraqui, S. H.; Karnik, M. A. Manganese triacetate mediated oxidation of Hantzsch 1,4-dihydropyridines to pyridines[J]. Tetrahedron Lett. 1999, 40 (1), 21-24.
[114] Anniyappan, M.; Muralidharan, D.; Perumal, P. T. A novel application of the oxidizing properties of urea nitrate and peroxydisulfate-cobalt(II): aromatization of NAD(P)H model Hantzsch 1,4-dihydropyridines[J]. Tetrahedron. 2002, 58, 5069-5073.
[115] Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature[J]. Tetrahedron Lett. 2003, 44, 4129-4131.
[116] Heravi, M. M.; Behbahani, F. K.; Oskooie, H. A.; Shoar, R. H. Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid[J]. Tetrahedron Lett. 2005, 46, 2775-2777.
[117] Moghadam, M.; Nasr-Esfahani, M.; Tangestaninejadb, S.; Mirkhanib, V. Mild and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by a new polystyrene-bound Mn(TPP)Cl[J]. Bioorganic & Med. Chem. Lett. 2006, 16, 2026- 2030.
[118] Han, B.; Liu, Z. G.; Liu, Q.; Yang, L.; Liu, Z. L.; Yu, W. An efficient aerobic oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines[J]. Tetrahedron. 2006, 62, 2492-2496.
[119] Chai, L. Z.; Zhao, Y. K.; Sheng, Q. J.; Liu, Z. Q. Aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines with HIO3 and I2O5 in water[J]. Tetrahedron Lett. 2006, 47, 9283-9285.
[120] Nasr-Esfahani, M.; Moghadam, M.; Tangestaninejad, S.; Mirkhanib, V.; Momenic, A. R. Rapid and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by manganese (III) Schiff base complexes[J]. Bioorganic & Med. Chem. 2006, 14, 2720-2724.
[121] (a) Sengupta, A. K.; Gupta, A. A. Indian J. Chem. [J]. 1983, 22B, 263-266. (b) 刘方明, 王宝雷, 李燕萍. 1,3-偶极环加成合成新型含 2-苯基-1,2,3-三唑基-1,5-苯并硫氮杂 噁二唑并合衍生物[J]. 高等学校化学学报. 2002, 23 (11), 2097-2101.
[122] 胡亮, 黄培池. 5-甲基-1-芳基-1 ,2 ,3-三唑衍生物的合成研究[J]. 化工技术与开发. 2006, 35 (10), 7-9.
[123] (a) Bochis, R. J.; Chabala, J. C.; Harris, E.; et al . Benzylated 1,2,3-triazoles as antioccidio tats [J]. J. Med. Chem. 1991, 34 (9), 2843-2852. (b) 张自义,刘莹,杨世琰,等. 5-醛胺基-1-芳基-1, 2, 3-连三唑[2, 4-d ]-嘧啶-4-酮类衍生物的合成和抗菌性能[J]. 高等学校化学学报. 1991, 12 (10), 1344-1348.
[124] 王彪. 原油降凝剂发展概况[J]. 精细石油化工. 1989, 32 (5), 43-53.
[125] 胡军. 降凝剂分子结构与分子设计[D]. 上海:华东理工大学, 1992.
[126] 郭翠梨, 张金利, 王一平.柴油低温流动改进剂的研究进展[J]. 化学工业与工程.1999, 16 (3), 157-162.
[127] (a) Feldman N icho las. U S, 3 910 776. 1975-10-07. (b) Feldman N. U S, 3 847 561. 1974-11-12.
[128] (a)William, C. H. U S, 3 982 909. 1976-09-28. (b) Alexis, A. O. Mountainside N J. U S, 4 402 708.1983-09-06.
[129] (a) 汤建华, 徐立群, 潘浪胜. 原油降凝剂的研制与初步应用实验[J]. 精细石油化工. 2001, 5, 5-7. (b) 龚望欣, 容永源, 曹晖等. 柴油低温流动改进剂的合成方法及影响因素[J]. 石化技术, 2003, 10 (1), 53-56.
[130] 吕崖, 谈兵, 严正泽. 影响柴油低温流动改进剂作用的因素[J]. 华东理工大学学报. 2001, 27 (6), 593-596.
[131] 商红岩, 姜翠玉, 吴明铂, 韩哲茵. 柴油低温流动改进剂的研制与评价Ⅱ柴油低温动性改进剂组分之间的协同效应[J]. 燃料化学学报. 2000, 28 (3), 226-228.
[132] 张付生, 王彪, 谢慧专, 董丽坚,张怀斌. 原油族组成对原油加降凝剂处理效果的影响[J]. 油田化学. 1999, 16 (2), 171-174.
[133] 赵容祥, 曹祖兵, 岳坤霞, 王峰. 降凝剂的应用概况[J]. 当代化工. 2003, 32 (4), 55-57.
[134] (a) 王敏, 赵静, 张廷山, 于元章. 原油降凝剂及其在我国原油中的应用[J]. 现代化工. 2001, 21 (11), 65-68. (b)丁兴者. 降凝剂的溶液性质及降凝机理研究(D). 杭州:浙江大学高分子系, 1995.
[135] 王丽娟, 田军. 聚合物性原油降凝剂的作用机理及应用[J]. 精细石油化工. 1997, 5, 5-8.
[136] 龚望欣, 容永源, 曹晖. 柴油低温流动性改进剂的合成方法及影响因素[J]. 石油技术. 2003, 10 (1), 53-56.
[137] (a) Atwal, K. S.; Swanson, B. N.; Uenger, S. E. Dihydropyrimidine calcium channel blockers: 3-carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effecitive antihypertensive agent [J]. J . Med. Chem. 1991, 34 (2), 806-811. (b) Kappe, C. O.; Fablan, W. M. F. Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators: a compareson of ab initio, semiempirical and X-ray crystallographic studies[J]. Tetrahedron. 1997, 53 (8), 2803-2816.
[138] Atwal, K. S.; Rovnyak, G. C.; Reillyb, C. Substituted 1 ,4-dihydropyrimidines 3 : syn- thesis of selectively fictionalized 2-hetero-1 ,4-dihydropyrimidines[J] . J . Org. Chem. 1989, 54 (25), 5898-5907.
[139] Sinder, B. B.; Shi, Z. Biomimetic synthesis of ( ±)2crambines A ,B ,C1 and C2. Revision of the structure of crambines B and C1[J]. J . Org. Chem. 1993, 58 (15), 3828-3839.
[140] Liu, F. M.(刘方明); Cao, L. H.(曹玲华). J. Xinjiang Univ. (Nature Science Ed.)(新疆大学学报, 自然科学版)[J]. 1993, 10 (1), 70-72.
[141] 段长强等主编. 现代化学试剂手册[M]. 化学工业出版社, 1988.
[142] 江丰明. 原油对柴油低温流动性改进剂感受性影响的探讨[J]. 石油炼制与化工, 1999, 30 (10), 26-28.