摘要
多组分反应是指由三种或三种以上的反应物以一锅煮的反应方式形成一个包含所有组分主要结构片段的新化合物的过程,是一类重要的有机化学反应。由于其高度的原子经济性、收敛性和出色的产率等特性以及在新药设计与合成、组合化学和天然产物合成等方面的重要应用,一锅多组分反应的研究越来越受到合成化学家们的重视。
超声辐射在有机合成中的应用研究近年来发展非常迅速,同传统的合成方法相比,其具有反应条件温和,操作简便,反应速度快,产率高等优点,为在一般条件下难以进行或不可能实现的化学反应提供了一种新的途径。论文对超声波的作用原理及在有机化学中的应用做了简单介绍,综述了近年来超声辐射在多组分一锅法合成中的应用,利用超声辐射下的一锅法反应合成了四类含氮化合物并对其结构进行了表征。
在25~28oC超声辐射下,以芳香醛、芳香酮、乙酰氯和乙腈为原料,硫酸钴为催化剂,通过多组分一锅法高产率合成了β-乙酰氨基酮类化合物。考察了催化剂用量对反应的影响,并与传统的加热回流反应进行对照。结果表明,超声法的反应效果要明显优于传统的加热回流法。
在超声辐射和NaOH存在下,利用一锅法,由芳醛肟与芳基磺酰氯在室温CH2Cl2中反应15~60min合成相应的O-芳磺酰基芳醛肟,收率56%~94%。对影响反应的因素如反应物的用量、催化剂种类及超声频率等进行了研究。方法操作简便,反应条件温和,时间短,产率高,为同类化合物的合成提供了一种简便有效的方法。
以对甲苯磺酸为催化剂,在乙醇溶剂中,由1-哌啶基-1,3-丁二酮、芳香醛和硫脲在室温超声辐射下,通过三组分一锅法有效地合成了系列含哌啶酰胺基的2-硫代-二氢嘧啶衍生物。反应时间1~2h,产物收率81%~91%,与传统的加热回流方法对比,反应时间明显缩短,产物收率高。
在超声辐射和十二烷基苯磺酸催化下,利用三组分一锅法由靛红酸酐、芳香醛和胺在水介质中合成了系列2,3-二取代-2,3-二氢喹唑啉-4(1H)-酮衍生物,反应温度40~42oC,反应时间1~2h,收率80%~92%。本方法操作和处理步骤简便,反应条件温和,避免使用有机溶剂,对环境友好。
Multi-component reactions are an important class of organic synthesis reaction, bywhich three or more reactants can form a compound containing the main structural fragmentof all components with one-pot method. Because of its high atom economy, convergence,excellent yield and the important applications in design and synthesis of new drug,combinatorial chemistry and synthesis of natural products, the study of one-potmulti-component reactions are getting more and more attention to the synthetic chemists.
In recent years, the application of ultrasound irradiation in organic synthesis developedrapidly. Compared with traditional methods, many organic reactions can be carried out undermild conditions, simple operation, in short reaction time with high yield under ultrasoundirradiation. It is a more versatile and facile in many types of chemical reactions, especially thereactions difficult or impossible to occur under normal conditions. In this paper, the principleof sonochemistry and some applications in organic synthesis were introduced, and theapplications of ultrasound in one-pot multi-component reactions were reviewed. Four kindsof nitrogenous compounds were syntheisized by one-pot synthesis under ultrasoundirradiation and characterized by their spectral data.
Ultrasound-promoted synthesis of β-acetamido ketones catalyzed by cobalt sulfateheptahydrate via one-pot multi-component reaction coupling of aromatic aldehyde,acetophenone and acetyl chloride in acetonitrile was carried out in excellent yields at25~28oC. The effect of the amount of the catalyst on the reaction was investigated, and the resultsunder different conditions were compared. It indicated that the results of the reaction underultrasound irradiation were obviously superior to those under reflux condition.
One-pot synthesis of O-arylsulfonyl arylaldoximes was carried out in56%~94%yieldswithin15~60min via the condensation of arylaldoxime with aromatic sulfonyl chloride in thepresence of sodium hydroxide at room temperature in dichloromethane under ultrasoundirradiation. The effect factors on the reaction such as the molar ratio of the reactant, the kindsof catalyst, and the frequency of ultrasound irradiation were studied. The advantages of this methodology are convenient operation, mild conditions, short reaction times, and high yields.It provides a simple and efficient method for the similar compounds.
A convenient and efficient one-pot synthesis of2-thioxo-dihydropyrimidine derivativesbearing piperidinylamide moiety was carried out in81%~91%yields within1~2h via thecondensation of1-(piperidin-1-yl)butane-1,3-dione with aromatic aldehyde and thiourea inethanol catalyzed by p-toluenesulfonic acid at room temperature under ultrasound irradiation.Comparing with the results under traditional refluxing conditions, the advantages of thismethodology are shorter reaction times and higher yields.
A series of2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-one derivatives weresynthesized in80%~92%yields within1~2h by one-pot three-component condensation ofisatoic anhydride, aromatic aldehyde and amine using dodecylbenzenesulfonic acid ascatalyst in aqueous medium at40~42oC under ultrasound irradiation. Simple experimentaland work-up procedures, mild reaction conditions, avoid the use of organic solvents, andfriendly to environment are the salient features of this protocol.
引文
[1](a) Weber L. The application of multi-component reactions in drug discovery[J]. Curr. Med. Chem.,2002,9(23),2085-2093;(b) Musonda C.C., Taylor D., Lehman J., Gut J., Rosenthal P.J., Chibale K. Application ofmulti-component reactions to antimalarial drug discovery. Part1: Parallel synthesis and antiplasmodialactivity of new4-aminoquinoline Ugi adducts[J]. Bio. Med. Chem. Lett.,2004,14(15),3901-3905.
[2](a) Ugi I. Recent progress in the chemistry of multicomponent reactions[J]. Pure Appl. Chem.,2001,73(1),187-191;(b) Posner G.H. Multicomponent one-pot annulations forming three to six bonds[J]. Chem. Rev.,1986,86(5),831-844.
[3] Strecker A. Justus Liebigs Ann. Chem.1850,75,27-45.
[4](a) Passerini M. Isonitriles. I. Compound of p-isonitrileazobenzene with acetone and acetic acid[J].Gazz. Chim. Ital,1921,51,126-129;(b) Passerini M. Isonitriles.(II). Compounds with aldehydes or ketones and monobasic organicacids[J]. Gazz. Chim. Ital.1921,51,181-188.
[5](a) Ugi I., Meyr R., Lipinski M., Bodesheim F., Rosendahl F. Cyclohexyl isocyanide[J]. Org. Synth.,1961,13;(b) Ugi I. Isonitrile II. Reaction of isonitriles with carbonyl compounds, amines, and hydrazoic acid[J].Chem. Ber.,1961,94(3),734-742.
[6](a) Ugi I., D mling A., H rl W. Multicomponent reactions in organic chemistry[J]. Endeavour,1994,18(3),115-122;(b) D mling A., Ugi I. The seven-component reaction[J]. Angew. Chem. Int. Ed.,1993,32(4),563-564;(c) Weber L., Wallbaum S., Broger C., Gubernator K. Optimization of the biological activity ofcombinatorial compound libraries by a genetic algorithm[J]. Angew. Chem. Int. Ed.,1995,34(20),2280-2282;(d) Weber L. Multi-component reactions and evolutionary chemistry[J]. Drug Discovery Today,2002,7(2),143-147;(e) Muravyova E.A., Shishkina S.V., Musatov V. I., Knyazeva I.V., Shishkin O.V., Desenko S.M.,Chebanov V.A. Chemoselectivity of multicomponent condensations of barbituric acids,5-aminopyrazoles, and aldehydes[J]. Synthesis,2009,(8),1375-1385.
[7]刘丽华.多组分反应研究现状[J].化工中间体,2012,9(2),1-5.
[8](a) Ganem B. Strategies for Innovation in Multicomponent Reaction Design[J]. Acc. Chem. Res.,2009,42(3),463-472;(b) Kalinski C., Lemoine H., Schmidt J., Burdack C., Kolb J., Umkehrer M., Ross G. Multicomponentreactions as a powerful tool for generic drug synthesis[J]. Synthesis,2008,(24),4007-4011;(c) Weber L., Illgen K., Almstetter M. Discovery of new multi component reactions withcombinatorial methods[J]. Synlett,1999,(3),366-374;(d) Tietze L.F., Evers H., T pken E. A novel concept in combinatorial chemistry in solution with theadvantages of solid-phase synthesis: Formation of N-betaines by multicomponent domino reactions[J].Angew. Chem. Int. Ed.,2001,40(5),903-905;(e) Tietze L F, Evers H, T pken E. A novel concept for combinatorial chemistry in solution: Synthesisof highly substituted pyrrolidines by multicomponent domino reactions[J]. Helv. Chim. Acta.,2002,85(12),4200-4205;(f) Zeng L.Y., Cai C. Iodine catalyzed one-pot multicomponent synthesis of a library of compoundscontaining tetrazolo [1,5-a] pyrimidine core[J]. J. Comb. Chem.,2009,12(1),35-40;(g) Jiang B, Xu M. Highly enantioselective construction of fused pyrrolidine systems that contain aquaternary stereocenter: concise formal synthesis of (+)-conessine[J]. Angew. Chem. Int. Ed.,2004,43(19),2543-2546.
[9] Saini A., Kumar S., Sandhu J.S. Hantzsch reaction: Recent advances in Hantzsch1,4-dihydropyridines[J]. J. Sci. Ind. Res.,2008,67,95-111.
[10] Vdovina S.V, Mamedov V.A. New potential of the classical Biginelli reaction[J]. Russ. Chem. Rev.,2008,77(12),1017-1054.
[11] Ting A, Schaus S.E. Organocatalytic asymmetric Mannich reactions: new methodology, catalyst design,and synthetic applications[J]. Eur. J. Org. Chem.,2007,(35),5797-5815.
[12](a) Mason T.J. Practical Sonochemistry[M]. Ellis Horwood Limited: New York,1991;(b)冯若,李化茂.声化学及其应用[M].安徽科学技术出版社,合肥,1992;(c) Mason T J. Ultrasound in synthetic organic chemistry[J]. Chem. Soc. Rev.,1997,26(6),443-451;(d) Mamaghani M., Dastmard S. An efficient ultrasound-promoted synthesis of the Baylis-Hillmanadducts catalyzed by imidazole and L-proline[J]. Ultrason. Sonochem.,2009,16(4),445-447.
[13]贾卫国,张鹏,刘振荣,李慧芳,杨奇,王君.超声化学的研究与应用[J].辽宁大学学报自然科学版,2002,29(3),198-202.
[14] Rechards W.T., Loomis A.L. The chemical effects of high frequency sound waves i. A preliminarysurvey[J]. J. Am. Chem. Soc.,1927,49(12),3086-3100.
[15] Porfer C.W., Young L. A molecular rearrangement induced by ultrasonic waves[J]. J. Am. Chem. Soc.,1938,60(6),1497-1500.
[16] Neppiras E.A.“Acoustic Cavitation”, Physics Reports-Review Section of Physics Letters,1980,61(3),159-251.
[17](a) Flint E.B., Suslick K.S. The temperature of cavitation[J]. Science,1991,253,1397-1399;(b) Suslick K.S. Sonochemistry[J]. Science,1990,247,1439-1445.
[18](a) Luche J.L. Synthetic Organic Sonochemistry[M], Plenum Press: New York,1998;(b) Li J.T., Wang S.X., Chen G.F., Li T.S. Some applications of ultrasound irradiation in organicsynthesis[J]. Curr. Org. Synth.,2005,2(3),415-436;(c) Memarian H.R., Farhadi A., Sabzyan H. Ultrasound-assisted dehydrogenation of5-acetyl-3,4-dihydropyrimidin-2(1H)-ones[J]. Ultrason. Sonochem.,2010,17(3),579-586;(d) Mantu D., Moldoveanu C., Nicolescu A., Deleanu C., Mangalagiu I.I. A facile synthesis ofpyridazinone derivatives under ultrasonic irradiation[J]. Ultrason. Sonochem.,2009,16(4),452-454;(e) Li J.T., Sun M.X., He G.Y., Xu X.Y. Efficient and green synthesis of bis(indolyl) methanescatalyzed by ABS in aqueous media under ultrasound irradiation[J]. Ultrason. Sonochem.,2011,18(1),412-414.
[19] Li J.T., Liu X.F. An efficient and practical synthesis of2,3-epoxyl-1,3-diaryl-1-propanone bycombination of phase transfer catalyst and ultrasound irradiation[J]. Ultrason. Sonochem.,2008,15(4),330-333.
[20] Li J.T., Liu X.R., Liu X.F. Oxidative cleavage of hydrobenzoin by ACC/silica gel under ultrasoundirradiation[J]. Ultrason. Sonochem.,2009,16(1),4-6.
[21] Li J.T., Liu X.R., Wang W.F. An efficient oxidation of benzoins to benzils by ACC/Silica gel underultrasound irradiation[J]. Ultrason. Sonochem.,2009,16(3),331-333.
[22] Gamble A.B., Gamer J., Gordon C.P. Aryl nitro reduction with iron powder or stannous chloride underultrasonic irradiation[J]. Synth. Commun.,2007,37(16),2777-2786.
[23] Peng Y.Q., Zhong W.J., Song G.H. Efficient and mild room temperature reduction of benzophenonesunder ultrasound irradiation[J]. Ultrason. Sonochem.,2005,12(3),169-172.
[24] Tobia D., Rickborn B. Stereochemistry of lithium dialkylamide-induced1,4-eliminations leading tosubstituted isobenzofurans[J]. J. Org. Chem.,1986,51(20),3849-3858.
[25] Li J.T., Lin Z.P. An efficient and practical synthesis of2-((1H-indol-3-yl)(aryl)methyl)malononitrilesunder ultrasound irradiation[J]. Ultrason. Sonochem.,2008,15(4),265-268.
[26] Wang S.X., Li X.W., Li J.T. Synthesis of N-alkoxyphthalimides under ultrasound irradiation[J].Ultrason. Sonochem.,2008,15(1),33-36.
[27] Koyama J., Sugita Y., Suzuta Y. Thermolysis of oxime O-allyl ethers: a new method for pyridinesynthesis[J]. Chem. Pharm. Bull.,1983,31(8),2601-2606.
[28] Leite A.C.L., Moreira D.R.M., Coelho L.C.D. Synthesis of aryl-hydrazones via ultrasound irradiationin aqueous medium[J]. Tetrahedron Lett.,2008,49(9),1538-1541.
[29] Pereira M.P., Stefani H.A., Guzen K.P. Improved synthesis of benzotriazoles and1-acylbenzotriazolesby ultrasound irradiation[J]. Lett. Org. Chem.,2007,4(1),43-46.
[30](a) Klaus S., Hübner S., Neumann H., Strübing D., Wangelin A.J., G rdes D., Beller M. Secondgeneration protocol for multicomponent coupling reactions of aldehydes, amides and dienophiles[J].Adv. Synth. Catal.,2004,346(8),970-978;(b) Ramón D.J., Yus M. Asymmetric multicomponent reactions (AMCRs): the new frontier[J]. Angew.Chem. Int. Ed.,2005,44(11),1602-1634;(c) Nishiyama Y., Katahira C., Sonoda N., A new method for the synthesis of1,3-oxathiolan-2-ones bythe reaction of epoxides with sulfur and carbon monoxide[J]. Tetrahedron Lett.,2004,45(46),8539-8540;(d) Tu S.J., Jiang B., Jia R.H., Zhang J.Y., Zhang Y. An efficient and expeditious microwave-assistedsynthesis of4-azafluorenones via a multi-component reaction[J]. Tetrahedron Lett.,2007,48(8),1369-1374;(e) Yonggui C., Steven T.S., Jean M.J.F. One-pot multi-component asymmetric Cascade reactionscatalyzed by soluble star polymers with highly branched non-interpentrating catalytic cores[J]. J. Am.Chem. Soc.,2008,130(20),6322-6323;(f) Kumar A., Sharma S., Maurya R.A. A novel multi-component reaction of indole, formaldehyde,and tertiary aromatic amines[J]. Tetrahedron Lett.,2009,50(43),5937-5940;(g) Li J.T., Chen B.H., Li Y.W. and Sun X.L. Efficient improved synthesis of2-aryl-4,5-diphenylimidazole by heating[J]. Int. J. Adv. Pharm. Bio. Chem.,2012,1(3),287-292.[31](a) Martins M.A.P., Frizzo C.P., Moreira D.N., Zanatta N., Bonacorso H.G. Ionic liquids inheterocyclic synthesis[J]. Chem. Rev.,2008,108(6),2015-2017;(b) Chebanov V.A, Desenko S.M. Multicomponent heterocyclization reactions with controlledselectivity (Review)[J]. Chem. Heter. Comp.,2012,48(4),566-583;(c) 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 aminoazoles, arylpyruvic acids andaldehydes with controlled chemoselectivity[J]. Tetrahedron,2008,64(49),11041-11049.
[32](a) D'Souzaa D.M., Müller T.J.J. Multi-component syntheses of heterocycles by transition-metalcatalysis[J]. Chem. Soc. Rev.,2007,36(7),1095-1108;(b) Heck S., D mling A. A versatile multi-component one-pot thiazole synthesis[J]. Synlett.,2000,(3),424-426;(c) Gu Y. Multicomponent reactions in unconventional solvents: state of the art[J]. Green Chem.,2012,14(8),2091-2128;(d) Climent M.J., Corma A., Iborra S. Homogeneous and heterogeneous catalysts for multicomponentreactions[J]. RSC Adv.,2012,2(1),16-58;(e) Graaff C., Ruijter E., Orru R.V.A. Recent developments in asymmetric multicomponentreactions[J]. Chem. Soc. Rev.,2012,41(10),3969-4009;(f) Chen L, Li Y.Q., Huang X.J., Zheng W.J. N,N-dimethylamino-functionalized basic ionic liquidcatalyzed one-pot multicomponent reaction for the synthesis of4H-benzo[b]pyran derivatives undersolvent-free condition[J]. Heteroat. Chem.,2009,20(2),91-94;(g) Cella R., Stefani H.A. Ultrasound in heterocycles chemistry[J]. Tetrahedron,2009,65(13),2619-2641.
[33] Kappe, C.O.100Years of the Binginelli dihydropyrimidie syntheisis[J]. Tetrahedron,1993,49(32),6937-6963.
[34](a) Li J.T., Han J.F., Yang J.H., Li T.S. An efficient synthesis of3,4-dihydropyrimidin-2-onescatalyzed by NH2SO3H under ultrasound irradiation[J]. Ultrason. Sonochem.,2003,10(2),119-122;(b)孙淑琴,李英俊,张治广,周晓霞.超声波辐射下3,4-二氢嘧啶-2(1H)-酮的合成[J].辽宁师范大学学报(自然科学版),2011,34(4),494-497.
[35] Mandhane P.G., Joshi R.S., Nagargoje D.R., Gill C.H. An efficient synthesis of3,4-dihydropyrimidin-2(1H)-ones catalyzed by thiamine hydrochloride in water under ultrasoundirradiation[J]. Tetrahedron Lett.,2010,51(23),3138-3140.
[36] Kumar H., Parmar A. Ultrasound promoted ZrCl4catalyzed rapid synthesis of substituted1,2,3,4-tetrahydropyrimidine-2-ones in solvent or dry media[J]. Ultrason. Sonochem.,2008,15(2),129-132.
[37] Li J.T., Lin Z.P., Han J.F., Li T.S. One-pot synthesis of4-oxo-2-thioxohexahydropyrimidinescatalyzed by potassium carbonate under ultrasound[J]. Synth. Commun.,2004,34(14),2623-2631.
[38](a) Wang S.X., Li J.T., Yang W.Z., Li T.S. Synthesis of ethyl α-cyanocinnamates catalyzed byKF-Al2O3under ultrasound irradiation[J]. Ultrason. Sonochem.,2002,9(3),159-161;(b) Garcia N.J.L., Lorente A., Soto J.L. Synthesis of heterocyclic compounds XXII. Preparation of6-aryl-2-thioxopyrimidines[J]. Heterocycles,1982,19,305-311.
[39] Stefani H.A., Oliveira C.B., Almeida R.B. Dihydropyrimidin-(2H)-ones obtained by ultrasoundirradiation: a new class of potential antioxidant agents[J]. Eur. J. Med. Chem.,2006,41(4),513-518.
[40]李记太,韩俊芬,蔺志平,李同双.超声辐射下4-氧代-2-硫代六氢嘧啶的合成[J].有机化学,2004,24(6),675-679.
[41](a) Dadhania A.N., Patel V.K., Raval D.K. A convenient and efficient protocol for the one potsynthesis of3,4-dihydropyrimidin-2-(1H)-ones catalyzed by ionic liquids under ultrasoundirradiation[J]. J. Braz. Chem. Soc.,2011,22(3),511-516;(b) Gholap A.R., Venkatesan K., Daniel T., Lahoti R.J., Srinivasan K.V. Ionic liquid promoted noveland efficient one pot synthesis of3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature underultrasound irradiation[J]. Green Chem.,2004,6(3),147-150.
[42]宛瑜,陈秀梅,张普,吴翚.超声辐射下2,4,5-三芳基咪唑的合成研究[J].徐州师范大学学报(自然科学版),2008,26(4),54-56.
[43] Nagargoje D., Mandhane P., Shingote S., Badadhe P., Gill C. Ultrasound assisted one pot synthesis ofimidazole derivatives using diethyl bromophosphate as an oxidant[J]. Ultrason. Sonochem.,2012,19(1),94-96.
[44] Shelke K.F., Sapkal S.B., Shingare M.S. Ultrasound-assisted one-pot synthesis of2,4,5-triarylimidazole derivatives catalyzed by ceric (IV) ammonium nitrate in aqueous media[J]. Chin.Chem. Lett.,2009,20(3),283-287.
[45] Shelke K.F., Sapkal S.B., Sonar S.S., Madje B.R., Shingate B.B., Shingare M.S. An Efficient synthesisof2,4,5-triaryl-1H-imidazole derivatives catalyzed by boric acid in aqueous media underultrasound-irradiation[J]. Bull. Korean Chem. Soc.,2009,30(5),1057-1060.
[46] Damavandi S. New approach to the multicomponent one-pot synthesis of2-aryl-1H-phenanthro [9,10-d] imidazoles[J]. Heter. Commun.,2011,17(1-2),79-81.
[47] Joshi R.S., Mandhane P.G., Dabhade S.K., Gill C.H. Tetrabutylammonium fluoride (TBAF) catalysedsynthesis of2-arylbenzimidazole in water under ultrasound irradiation[J]. J. Chin. Chem. Soc.,2010,57(6),1227-1231.
[48] Ruiz E., Rodriguez H., Coro J., Salfran E., Suarez M., Martinez-Alvarez R., Martin N.Ultrasound-assisted one-pot, four component synthesis of4-aryl3,4-dihydropyridone derivatives[J].Ultrason. Sonochem.,2011,18(1),32-36.
[49] Safari J., Banitaba S.H., Khalili S.D. Ultrasound-promoted an efficient method for one-pot synthesis of2-amino-4,6-diphenylnicotinonitriles in water: a rapid procedure without catalyst[J]. Ultrason.Sonochem.,2012,19(5),1061-1069.
[50] Heravi M.R.P., Fakhr F. Ultrasound-promoted synthesis of2-amino-6-(arylthio)-4-arylpyridine-3,5-dicarbonitriles using ZrOCl2·8H2O/NaNH2as the catalyst in the ionic liquid [bmim]BF4at roomtemperature[J]. Tetrahedron Lett.,2011,52(50),6779–6782.
[51] Wang S.X., Li Z.Y., Zhang J.C., Li J.T.. The solvent-free synthesis of1,4-dihydropyridines underultrasound irradiation without catalyst[J]. Ultrason. Sonochem.,2008,15(5),677-680.
[52] Li J.T., Xu W.Z., Yang L.C., Li T.S. One-Pot Synthesis of2-amino-4-aryl-3-carbalkoxy-7,7-dimethyl-5,6,7,8-tetrahydrobenzo[b]pyran derivatives catalyzed by KF/Basic Al2O3under ultrasoundirradiation[J]. Synth. Commun.,2004,34(24),4565-4571.
[53] Jin T.S., Xiao J.C., Wang S.J., Li T.S. Ultrasound-assisted synthesis of2-amino-2-chromenes withcetyltrimethylammonium bromide in aqueous media[J]. Ultrason. Sonochem.,2004,11(6),393-397.
[54] Li J.J., Li J., Fang J., Su W.K. Efficient one-pot condensation of β-naphthol, aldehydes, and cyclic1,3-dicarbonyl compounds catalyzed by p-TSA under solvent-free and sonication conditions[J]. Synth.Commun.,2010,40(7),1029-1039.
[55]李卓宁,高原,刘波,吕维中.超声辐射下2-氨基-7-甲基-4-芳基-5-氧代-4H,5H-吡喃并[4,3-b]吡喃-3-腈的“一锅法”合成[J].应用化学,2008,25(6),744-746.
[56] Banitaba S.H., Safari J., Khalili D. Ultrasound promoted one-pot synthesis of2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: A complementary ‘greenchemistry’ tool to organic synthesis[J]. Ultrason. Sonochem.,2013,20(1),401-407.
[57] Liu H., Zou Y., Hu Y., Shi D.Q. An efficient one-pot synthesis of dispiropyrrolidine derivativesthrough1,3-dipolar cycloaddition reactions under ultrasound irradiation[J]. J. Heterocyclic Chem.,2011,48(4),877-881.
[58] Azarifar D., Sheikh D. ZrOCl28H2O: An efficient, ecofriendly, and recyclable catalyst forultrasound-accelerated, one-pot, solvent-free synthesis of8-aryl-7,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-6-(5H)-one and4-aryl-3,4-dihydroquinolin-2(1H)-one derivatives[J]. Synth. Commun.,2013,43(18),2517-2526.
[59] Zhang D.N., Li J.T., Song Y.L., Liu H.M., Li H.Y. Efficient one-pot three-component synthesis ofN-(4-arylthiazol-2-yl) hydrazones in water under ultrasound irradiation[J]. Ultrason. Sonochem.,2012,19(3),475-478.
[60]李德富,袁明月,张英群,张冬暖,刘卉闵,杨旭哲.超声波辐射合成2-氨基噻唑衍生物[J].化学试剂,2011,33(5),463~465.
[61]李英俊,孙亚珍,靳焜,许永廷,孙淑琴.2,5-二取代-1,3,4-噻二唑衍生物的一锅法合成、结构表征及生物活性研究[J].有机化学,2008,28(6),1074-1078.
[62] Rouhani M., Ramazani A., Joo S,W., Hanifehpour Y. Very efficient and rapid catalyst-free one-potthree component synthesis of2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylate derivatives underultrasound irradiation[J]. Bull. Korean Chem. Soc.,2012,33(12),4127-4130.
[63] Bardajee G.R., Jafarpour F., Afsari H.S. ZrOCl28H2O: An efficient catalyst for rapid one-pot synthesisof3-carboxycoumarins under ultrasound irradiation in water[J]. Cent. Eur. J. Chem.,2010,8(2),370-374.
[64] Palmisano G., Tibiletti F., Penoni A., Colombo F., Tollari S., Garella D., Tagliapietra S., Cravotto G.Ultrasound-enhanced one-pot synthesis of3-(Het)arylmethyl-4-hydroxycoumarins in water[J].Ultrason. Sonochem.,2011,18(2),652-660.
[65] Khaligh N.G. Ultrasound-assisted one-pot synthesis of substituted coumarins catalyzed bypoly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst[J]. Ultrason.Sonochem.,2013,20(4),1062-1068.
[66] Li J.T., Sun S.F., Sun M.X. Improved synthesis of3-(dialkylaminomethyl)-indole in acetic acidaqueous solution under ultrasound irradiation[J]. Ultrason. Sonochem.,2011,18(1),42-44.
[67] Dandia A., Bhati D.S., Jain A.K., Sharma G.N. Ultrasound promoted clay catalyzed efficient and onepot synthesis of substituted oxindoles[J]. Ultrason. Sonochem.,2011,18(5),1143-1147.
[68] Suresh Babu A.R., Raghunathan R. Ultrasonic ssisted-silica mediated [3+2] cycloaddition ofazomethine ylides—a facile multicomponent one-pot synthesis of novel dispiroheterocycles[J].Tetrahedron Lett.,2007,48(38),6809-6813.
[69]赵新海,刘晨江,李燕萍.超声波促进离子液体中Biginelli一锅法合成苯并咪唑并[2,1-b]喹啉-6-酮[J].高等学校化学学报,2010,31(9),1769-1773.
[70] Zang H.J., Zhang Y., Zang Y.P., Cheng B.W. An efficient ultrasound-promoted method for theone-pot synthesis of7,10,11,12-tetrahydrobenzo[c]acridin-8-(9H)-one derivatives[J]. Ultrason.Sonochem.,2010,17(3),495-499.
[71] Zang H.J., Zhang Y., Mo Y.M., Cheng B.W. Ultrasound-promoted one-pot synthesis of7-aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8-(9H)-one derivatives[J]. Synth. Commun.,2011,41(21),3207-3214.
[72] Azarifar D., Sheikh D. Ultrasound-accelerated one-pot synthesis of N-acetyl-2-aryl-1,2-dihydro-4H-3,1-benzoxazin-4-ones[J]. Chem. Heter. Comp.,2011,47(9),1128-1136.
[73] Ablajan K., Kamil W., Tuoheti A., Sun W.F. An efficient three component one-pot synthesis of5-amino-7-aryl-7,8-dihydro-[1,2,4]triazolo[4,3-a]-pyrimidine-6-carbonitriles[J]. Molecules,2012,17(2),1860-1869.
[74] Al-Bogami A.S., Saleh T.S., Zayed E.M. Divergent reaction pathways for one-pot, three-componentsynthesis of novel4H-pyrano[3,2-h]quinolines under ultrasound irradiation[J]. Ultrason. Sonochem.,2013,20(5),1194-1202.
[75] Niralwad K.S., Shingate B.B., Shingare M.S. Ultrasound-assisted one-pot synthesis ofoctahydroquinazolinone derivatives catalyzed by acidic ionic liquid [tbmim]Cl2/AlCl3[J].J. Chin.Chem. Soc.,2010,57(1),89-92.
[76] Neuenfeldt P.D., Duval A.R., Drawanz B.B., Rosales P.F., Gomes C.R.B., Pereira C.M.P., Cunico W.Efficient sonochemical synthesis of thiazolidinones from piperonilamine[J]. Ultrason. Sonochem.,2011,18(1),65-67.
[77] Shukla G, Verma R K, Verma G K, Singh M.S. Solvent-free sonochemical one-pot three-componentsynthesis of2H-indazolo[2,1-b]phthalazine-1,6,11-triones and1H-pyrazolo[1,2-b]phthalazine-5,10-diones[J]. Tetrahedron Lett.,2011,52(52),7195-7198.
[78] Shekouhy M., Hasaninejad A. Ultrasound-promoted catalyst-free one-pot four component synthesis of2H-indazolo[2,1-b]phthalazine-triones in neutral ionic liquid1-butyl-3-methylimidazolium bromide[J].Ultrason. Sonochem.,2012,19(2),307-313.
[79] Nabid M.R., Rezaei S.J., Ghahremanzadeh R., Bazgir A. Ultrasound-assisted one-pot,three-component synthesis of1H-pyrazolo[1,2-b]phthalazine-5,10-diones[J]. Ultrason. Sonochem.,2010,17(1),159-161.
[80] Wang J., Bai X., Xu C., Wang Y., Lin W., Zou Y., Shi D. Ultrasound-promoted one-pot,three-component synthesis of spiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine] derivatives[J].Molecules,2012,17(7),8674-8686.
[81] Saleh T.S., Eldebss T.M., Albishri H.M. Ultrasound assisted one-pot, three-components synthesis ofpyrimido[1,2-a]benzimidazoles and pyrazolo[3,4-b]pyridines: A new access via phenylsulfonesynthon[J]. Ultrason. Sonochem,2012,19(1),49-55.
[82] Bazgir A., Ahadi S., Ghahremanzadeh R., Khavasi H.R., Mirzaei P. Ultrasound-assisted one-pot,three-component synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,6'(1'H)-diones in water[J].Ultrason. Sonochem.,2010,17(2),447-452.
[83] Nikpassand M., Mamaghani M., Shirini F., Tabatabaeian K. A convenient ultrasound-promotedregioselective synthesis of fused polycyclic4-aryl-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridines[J]. Ultrason. Sonochem.,2010,17(2),301-305.
[84]赵新海,刘晨江,李燕萍.超声波促进离子液体中Biginelli一锅法合成苯并咪唑并[2,1-b]喹啉-6-酮[J].高等学校化学学报,2010,31(9),1769-1773.
[85]王慧彦,邹毅,陶传洲.超声作用下四组分一锅法合成二氢吡喃并[2,3-c]吡唑衍生物[J].有机化学,2011,31(12),2161-2166.
[86] Ablajan K., Xiamuxi H. Efficient one-pot synthesis of β-unsaturated isoxazol-5-ones and pyrazol-5-ones under ultrasonic irradiation[J]. Synth. Commun.,2012,42(8),1128-1136.
[87] Wang S.X., Wang W., Li J.T. Synthesis of6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyran[2,3-c]pyrazole derivatives without catalyst under ultrasound irradiation[J]. E. J. Chem.,2005,2(7),121-125.
[88]金士波,李敬芬,孟跃.醇介质中超声波促进一锅法合成吡喃并[2,3-d]嘧啶衍生物[J].河南化工,2012,29(9),32-34.
[89]程青芳,许兴友,阮明杰,温艳玲,何晓姜,杨绪杰.超声辐射下水介质中三组分一锅合成吡喃并[2,3-d]嘧啶衍生物[J].有机化学,2009,29(7),1138-1141.
[90] Xia M., Lu Y.D. Ultrasound-assisted one-pot approach to alpha-amino phosphonates undersolvent-free and catalyst-free conditions[J]. Ultrason. Sonochem.,2007,14(2),235-240.
[91] Dar B., Singh A., Sahu A., Patidar P., Chakraborty A., Sharma M., Singh B. Catalyst and solvent-free,ultrasound promoted rapid protocol for the one-pot synthesis of α-aminophosphonates at roomtemperature[J]. Tetrahedron Lett.,2012,53(41),5497-5502.
[92] Kaboudin B., Fallahi M. Ultrasound-assisted one-pot synthesis of α-oxycarbanilinophosphonates via athree-component condensation of an aldehyde, diethyl phosphate and an isocyanate under solvent-freeconditions[J]. Tetrahedron Lett.,2011,52(33),4346-4348.
[93] Sreedhar B., Reddy P.S., Prakash B.V., Ravindra A. Ultrasound-assisted rapid and efficient synthesisof propargylamines[J]. Tetrahedron Lett.,2005,46(41),7019-7022.
[94] Patil S.B., Singh P.R., Surpur M.P., Samant S.D. Ultrasound-promoted synthesis of1-amidoalkyl-2-naphthols via a three-component condensation of2-naphthol, ureas/amides, and aldehydes,catalyzed by sulfamic acid under ambient conditions[J]. Ultrason. Sonochem.,2007,14(5),515–518.
[95] Enders D., Moser M., Geibel G., Laufer M.C. Diastereo-and enantioselective synthesis of differentlyN,O-protected1,3-amino alcohols with three neighbouring stereogenic centers[J]. Synthesis,2004,(12),2040-2046.
[96] Barluenga J., Viado A.L., Aguilar E., Fustero S., Olano B.1,3-Amino alcohols from4-amino-1-azadienes. Diastereo-and enantioselective approach to the four diastereoisomers of the N-terminal aminoacid component of nikkomycins B and BX[J]. J. Org. Chem.,1993,58(22),5972-5975.
[97] Kobinata K., Uramoto M., Nishii M., Kusakabe H., Nakamura G., Isono K. Neopolyoxins A, B, and C,new chitin synthetase inhibitors[J]. Agric. Biol. Chem.,1980,44(7),1709-1711.
[98](a) Darkin H.D., West R. A general reaction of amino acids. II[J]. J. Biol. Chem.,1928,78,745-746;(b) Buchanan G.L. The Dakin-West reaction[J]. Chem. Soc. Rev.,1988,17,91-109.
[99](a) Bhatia B., Reddy M.M., Iqbal J. Cobalt catalysed three component coupling involving ketones orketoesters, aldehyde and acetonotrile: a novel one pot synthesis of β-acetamido ketones[J]. J. Chem.Soc., Chem. Commun.,1994,(6),713-714;(b) Rao I.N., Prabhakaran E.N., Das S.K., Iqbal J. Cobalt-catalyzed one-pot three-componentcoupling route to β-acetamido carbonyl compounds: a general synthetic protocol for γ-lactams[J]. J.Org. Chem.,2003,68(10),4079-4082;(c) Bahulayan D., Das S.K., Iqbal J. Montmorillonite K10Clay: An efficient catalyst for the one-potstereoselective synthesis of β-acetamido ketones[J]. J. Org. Chem.,2003,68(14),5735-5738.
[100] Khan A.T., Choudhury L.H., Parvin T. CeCl3·7H2O: an efficient and reusable catalyst for thereparation of β-acetamido carbonyl compounds by multi-component reactions (MCRs)[J].Tetrahedron Lett.,2006,47(46),8137-8141.
[101] Khan A.T., Parvin T., Choudhury L.H. Iron(III) chloride-catalyzed convenient one-pot synthesis ofβ-acetamido carbonyl compounds[J]. Tetrahedron,2007,63(25),5593-5601.
[102] Ghosh R., Maiti S., Chakraborty A. ZrOCl2·8H2O: an efficient Lewis acid catalyst for the one-potmulticomponent synthesis of β-acetamido ketones[J]. Tetrahedron,2006,62(17),4059-4064.
[103] Maghsoodlou M.T., Hassankhani A., Shaterian H.R. Zinc oxide as an economical and efficientcatalyst for the one-pot preparation of β-acetamido ketones via a four-component condensationreaction[J]. Tetrahedron Lett.,2007,48(10),1729-1734.
[104] Shaterian H.R., Hosseinian A., Ghashang M. One-pot preparation of β-amido ketones/esters in athree-component condensation reaction using magnesium hydrogensulfate as an effective andreusable catalyst[J]. Can. J. Chem.,2008,86(5),376-383.
[105] Salama T.A., Elmorsy S.S., Khalil A.M., Ismail M. A. A SiCl4–ZnCl2induced general, mild andefficient one-pot, three-component synthesis of β-amido ketone libraries[J]. Tetrahedron Lett.,2007,48(35),6199-6203.
[106] Yadav J.S., SubbaReddy B., Shankar V.K. Copper(II) tetrafluoroborate as mild and versatile catalystfor the rapid synthesis of β-acetamido ketones and ketoesters via a three component reaction[J]. Org.Commun.,2008,(1),76-83.
[107] Mirjalili B.F., Bamonirib A., Zarchi M.A.K., Emtiazi H. Zr(HSO4)4/SiO2: An effectiveheterogeneous alternative for one-pot synthesis of β-acetamido ketones[J]. J. Iran. Chem. Soc.,2010,7(1),95-99.
[108] Das B., Srilatha M., Veeranjaneyulu B., Rao B.R. An efficient, one-pot, multicomponent synthesis ofβ-acetamido carbonyl compounds using cyanuric chloride in an aqueous medium[J]. Synthesis,2010,(5),803-806.
[109](a) Rafiee E., Shahbazi F., Joshaghani M. The silica supported H3PW12O40(a heteropoly acid) as anefficient and reusable catalyst for a one-pot synthesis of β-acetamido ketones by Dakin-Westreaction[J]. J. Mol. Catal. A: Chem.,2005,242(1-2),129-134;(b) Rafiee E., Torka F., Joshaghani M. Heteropoly acids as solid green Br nsted acids for a one-potsynthesis of β-acetamido ketones by Dakin-West reaction[J]. Bioorg. Med. Chem. Lett.,2006,16(5),1221-1226;(c) Heravi M.M., Ranjbar L., Derikvand F. H6P2W18O62: An efficient and reusable catalyst for one-potsynthesis of β-acetamido ketone and esters[J]. Catal. Commun.,2007,8(3),289-291;(d) Rafiee E., Paknezhad F., Shahebrahimi S., Joshaghani M., Eavani S., Rashidzadeh S. Acidcatalysis of different supported heteropoly acids for a one-pot synthesis of β-acetamido ketones[J]. J.Mol. Catal. A: Chem.,2008,282(1),92-98.
[110] Das B., Reddy K.R. Facile one-pot multicomponent synthesis of β-acetamido ketones withAmberlyst-15as heterogeneous catalyst[J]. Helv. Chim. Acta.,2006,89(12),3109-3111.
[111] Khodaei M.M., Khosropour A.R., Fattahpour P. A modified procedure for the Dakin-West reaction:an efficient and convenient method for a one-pot synthesis of β-acetamido ketones using silicasulfuric acid as catalyst[J]. Tetrahedron Lett.,2005,46(12),2105-2108.
[112] Davoodnia A., Heravi M.M., Rezaei-Daghigh L., Tavakoli-Hoseini N. Br nsted-acidic ionic liquid
[HO3S(CH2)4MIM][HSO4] as efficient and reusable catalyst for one-pot synthesis of β-acetamidoketones[J]. Monatsh. Chem.,2009,140(12),1499-1502.
[113](a) Mao H., Wan J.P., Pan Y.J. Facile and diastereoselective synthesis of β-acetamido ketones andketo esters via direct Mannich-type reaction[J]. Tetrahedron,2009,65(5),1026-1032;(b) Shinu V.S., Sheeja B., Purushothaman E., Bahulayan D. An efficient green MCR protocol for thestereoselective synthesis of β-acetamido ketones catalyzed by SelectfluorTM[J]. Tetrahedron Lett.,2009,50(34),4838-4843;(c) Nabid M.R., Rezaei S.J.T. Polyaniline-supported acid as an efficient and reusable catalyst for aone-pot synthesis of β-acetamido ketones via a four-component condensation reaction[J]. Appl. Catal.,A,2009,366(1),108-113.
[114] Wang M., Tian G.F., Song Z.G., Jiang H. Cobalt sulfate as a recyclable catalyst for chemoselectivesynthesis of diacetates from aldehydes[J]. Chem. Res. Chin. Univ.,2009,25,455-457.
[115]陆晓华.固体酸催化的多组分反应研究[D].苏州:苏州大学硕士学位论文,2008.
[116] Mohammadpoor-Baltork I., Moghadam M., Tangestaninejad S., Mirkhani V., Eskandari Z.Ultrasound promoted selective synthesis of2-aryl-5,6-dihydro-4H-1,3-oxazines catalyzed by K-10and KSF montmorillonite clays: A practical procedure under mild and solvent-free conditions[J].Ultrason. Sonochem.,2010,17(5),857-862.
[117] Hutchison G.I., Prager R.H., Ward A.D. Central nervous system active compounds. III*Thesynthesis of4-and6-substituted caprolactam derivatives by the Schmidt and Beckmannrearrangements[J]. Aust. J. Chem.,1980,33(11),2477-2486.
[118](a) Heldt W.Z. Beckmann Rearrangement. I. Syntheses of oxime p-toluenesulfonates and Beckmannrearrangement in acetic acid, methyl alcohol and chloroform[J]. J. Am. Chem. Soc.,1958,80(21),5880-5885;(b) Heldt W.Z. Beckmann rearrangement. II. Salt effects in the acetolysis of cyclopentanone andcyclohexanone oxime p-toluenesulfonate[J]. J. Am. Chem. Soc.,1958,80(22),5972-5978.
[119](a) Costa A., Mestres R., Riego J.M. Reactions on silica gel. Beckmann rearrangement of oximep-toluenesulfonates[J]. Synth. Commun.,1982,12(13),1003-1006;(b) Hattori K., Maruoka K., Yamamoto H. Beckmann rearrangement of oxime sulfonates by Grignardreagents[J]. Tetrahedron Lett.,1982,23(33),3395-3396.
[120] Hattori K., Matsumura Y., Miyazaki T., Maruoka K., Yamamoto H. Successive Beckmannrearrangement-alkylation sequence by organoaluminum reagents. Simple route to dl-pumiliotoxinC[J]. J. Am. Chem. Soc.,1981,103(24),7368-7370.
[121] Hatch M.J., Cram D.J. Observations on the mechanism and scope of the Neber rearrangemen[J]. J.Am. Chem. Soc.,1953,75(1),38-44.
[122](a) O’Brien C. The rearrangement of ketoxime O-sulfonates to amino ketones (the Neberrearrangement)[J]. Chem. Rev.,1964,64(2),81-89;(b) Hyatt J.A. Neber rearrangement of amidoxime sulfonates. Syntheisi of2-amino-1-azirines[J]. J.Org. Chem.,1981,46(20),3953-3955;(c) Ooi T., Takahashi M., Doda K., Maruoka K. Asymmetric induction in the Neber rearrangement ofsimple ketoxime sulfonates under phase-transfer conditions: experimental evidence for theparticipation of an anionic pathway[J]. J. Am. Chem. Soc.,2002,124(26),7640-7641.
[123] Al-Awadi N.A., Elnagdi M.H., Kaul K., Ilingovan S., El-Dusouqui, O.M.E. Kinetics and mechanismof pyrolysis of sulphonyl hydrazones and oximes. Part1. Contribution to reactivity from hydrazoneHN-N and oxime O-N bond polarity[J]. Tetrahedron,1998,54(18),4633-4640.
[124] Al-Awadi N.A., Elnagdi M.H., Kaul K., Ilingovan S., El-Dusouqui O.M.E. Kinetics and mechanismof pyrolysis of sulphonyl hydrazones and oximes. Part2. Structural effects and molecular reactivity[J].J. Phys. Org. Chem.,1999,12(8),654-658.
[125] Crawford R.J., Woo C. The conversion of meta-and para-substituted benzaldoxime arenesulfonatesto nitriles[J]. Can. J. Chem.,1965,43(5),1534-1544.
[126] Kitamura M., Chiba S., Narasaka K. Synthesis of primary amines and N-methylamines by theelectrophilic amination of Grignard reagents with2-imidazolidinone O-sulfonyloxime[J]. Bull. Chem.Soc. Jpn.,2003,76(5),1063-1070.
[127] Hassner A., Patchornik G., Pradhan T.K., Kumareswaran R. Intermolecular electrophilic O-aminationof alcohols[J]. J. Org. Chem.,2007,72(2),658-661.
[128]邓桂胜,莫宏华,罗景,汤力.无碱条件下由芳香醛肟和磺酰氯制备O-磺酰基芳香醛肟[J].有机化学,2012,32(11),2177-2180.
[129](a) Li J.T., Li X.L. An efficient and practical synthesis of methylene dioximes by combination ofultrasound and phase transfer catalyst[J]. Ultrason. Sonochem.,2007,14(6),677-679;(b)李记太,李晓亮,刘献锋,马洁洁.超声辐射和相转移催化下肟苄醚的合成[J].有机化学,2008,28(4),628-631.
[130] Li J.T., Li X.L., Li T.S. Synthesis of oximes under ultrasound irradiation[J]. Ultrason. Sonochem.,2006,13(3),200-202.
[131](a) McNulty J., Steere J.A., Wolf S. The ultrasound promoted Knoevenagel condensation of aromaticaldehydes[J]. Tetrahedron lett.,1998,39(44),8013-8016;(b) Mason T. J., Peters, D. Practical sonochemistry. Power ultrasound uses and applications,2nded[M]. Ellis Horwood: New York,2002.
[132](a) Louisnard O. A simple model of ultrasound propagation in a cavitating liquid. Part I: Theory,nonlinear attenuation and traveling wave generation[J]. Ultrason. Sonochem.,2012,19(1),56-65;(b) Louisnard O. A simple model of ultrasound propagation in a cavitating liquid. Part II: PrimaryBjerknes force and bubble structures[J]. Ultrason. Sonochem.,2012,19(1),66-76.
[133](a) Kappe C.O. Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an olddog[J]. Acc. Chem. Res.,2000,33(12),879-888;(b) Kappe C.O. Biologically active dihydropyrimidones of the Biginelli-type—a literature survey[J].Eur. J. Med. Chem.,2000,35(12),1043-1052;(c) Wan J.P., Liu Y.Y. Synthesis of dihydropyrimidinones and thiones by multicomponent reactions:strategies beyond the classical Biginelli reaction[J]. Synthesis,2010,(23),3943-3953.[134](a) Kappe C.O.4-Aryldihydropyrimidines via the Biginelli condensation: aza-analogs of nifedipine-type calcium channel modulators[J]. Molecules,1998,3(1),1-9;(b) Atwal K.S., Rovnyak G.C., Schwartz J., Moreland S., Hedberg A., Gougoutas J.Z., Malley M.F.,Floyd D.M. Dihydropyrimidine calcium channel blockers:2-heterosubstituted4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines[J]. J. Med. Chem.,1990,33(5),1510-1515;(c) Chikhale R.V., Bhole R.P., Khedekar P.B., Bhusari K.P. Synthesis and pharmacologicalinvestigation of3-(substituted1-phenylethanone)-4-(substituted phenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates[J]. Eur. J. Med. Chem.,2009,44(9),3645-3653;(d) Kappe C.O., Fabian W.M.F., Semones M.A. Conformational analysis of4-aryl-dihydropyrimidinecalcium channel modulators. A comparison of ab Initio, semiempirical and X-ray crystallographicstudies[J]. Tetrahedron,1997,53(8),2803-2816.
[135](a) Mokale S.N., Shinde S.S., Elgire R.D., Sangshetti J.N., Shinde D.B. Synthesis andanti-inflammatory activity of some3-(4,6-disubtituted-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid derivatives[J]. Bioorg. Med. Chem. Lett.,2010,20(15),4424-4426;(b) Bahekar S.S., Shinde D.B. Synthesis and anti-inflammatory activity of some [4,6-(4-substitutedaryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]-acetic acid derivatives[J]. Bioorg. Med. Chem. Lett.,2004,14(7),1733-1736.[136](a) Alam O., Khan S.A., Siddiqui N., Ahsan W., Verma S.P., Gilani S.J. Antihypertensive activity ofnewer1,4-dihydro-5-pyrimidine carboxamides: synthesis and pharmacological evaluation[J]. Eur. J.Med. Chem.,2010,45(11),5113-5119;(b) Chikhale R.V., Bhole R.P., Khedekar P.B., Bhusari K.P. Synthesis and pharmacologicalinvestigation of3-(substituted1-phenylethanone)-4-(substituted phenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates[J]. Eur. J. Med. Chem.,2009,44(9),3645-3653.
[137](a) Kumar B.R.P., Sankar G., Baig R.B.N., Chandrashekaran S. Novel Biginelli dihydropyrimidineswith potential anticancer activity: a parallel synthesis and CoMSIA study[J]. Eur. J. Med. Chem.,2009,44(10),4192-4198;(b) Holla B.S., Rao B.S., Sarojini B.K., Akberali P.M. One pot synthesis of thiazolodihydropyrimidinones and evaluation of their anticancer activity[J]. Eur. J. Med. Chem.,2004,39(9),777-783.
[138](a) Desai B., Sureja D., Naliapara Y., Shah A., Saxena A.K. Synthesis and QSAR studies of4-substituted phenyl-2,6-dimethyl-3,5-bis-N-(substituted Phenyl)carbamoyl-1,4-dihydropyridines aspotential antitubercular Agents[J]. Bio. Med. Chem.,2001,9(8),1993-1998;(b) Yadlapalli R.K., Chourasia O.P., Vemuri K., Sritharan M., Perali R.S. Synthesis and in vitroanticancer and antitubercular activity of diarylpyrazole ligated dihydropyrimidines possessinglipophilic carbamoyl group[J]. Bio. Med. Chem. Lett.,2012,22(8),2708-2711.
[139] Wipf P., Cunningham A. A solid phase protocol of the Biginelli dihydropyrimidine synthesis suitablefor combinatorial chemistry[J]. Tetrahedron Lett.,1995,36(43),7819-7822.
[140](a) Barrow J.C., Nantermet P.G., Selnick H.G., Glass K.L., Rittle K.E., Gilbert K.F., Steele T.G.,Homnick C.F., Freidinger R.M., Ransom R.W., Kling P., Reiss D., Broten T.P., Schorn T.W., ChangR.S.L., O’Malley S.S., Olah T.V., Ellis J.D., Barrish A., Kassahun K., Leppert P., Nagarathnam D.,and Forray C. In vitro and in vivo evaluation of dihydropyrimidinone C-5amides as potent andselective α1Areceptor antagonists for the treatment of benign prostatic hyperplasia[J]. J. Med. Chem.,2000,43(14),2703-2718;(b) Lagu B., Tian D., Chiu G., Nagarathnam D., Fang J., Shen Q., Forray C., Ransom R.W., ChangR.S.L., Vyas K.P., Zhang K.Y., Gluchowski C. Synthesis and evaluation of furo[3,4-d]pyrimidinonesas selective α1a-adrenergic receptor antagonists[J]. Bioorg. Med. Chem. Lett.,2000,10(2),175-178;(c) Barrow J.C., Glass K.L., Selnick H.G., Freidinger R.M., Chang R.S.L., O’Malley S.S., Woyden C.Preparation and evaluation of1,3-diaminocyclopentane-linked dihydropyrimidinone derivatives asselective α1a-receptor antagonists[J]. Bioorg. Med. Chem. Lett.,2000,10(17),1917-1920.
[141] Blackburn C., Guan B., Brown J., Cullis C., Condon S.M., Jenkins T.J., Peluso S., Ye Y., GimenoR.E., Punreddy S., Sun Y., Wu H., Hubbard B., Kaushik V., Tummino P., Sanchetti P., Sun D.Y.,Daniels T., Tozzo E., Balani S.K., Raman P. Identification and characterization of4-aryl-3,4-dihydropyrimidin-2(1H)-ones as inhibitors of the fatty acid transporter FATP4[J]. Bio. Med. Chem.Lett.,2006,16(13),3504-3509.
[142] Kaan H.Y., Ulaganathan V., Rath O., Prokopcova H., Dallinger D., Kappe C.O., Kozielski F.Structural basis for inhibition of Eg5by dihydropyrimidines: stereoselectivity of antimitotic inhibitorsenastron, dimethylenastron and fluorastrol[J]. J. Med. Chem.,2010,53(15),5676-5683.
[143](a) Heys L., Moore C.G., Murphy P.J. The guanidine metabolites of Ptilocaulisspiculifer and relatedcompounds: isolation and synthesis[J]. Chem. Soc. Rev.,2000,29(1),57-67;(b) Aron Z.D., Overman L.E. The tethered Biginelli condensation in natural product synthesis[J].Chem. Commun.,2004,(3),253-265;(c) Patil A.D., Kumar N.V., Kokke W.C., Bean M.F., Freyer A.J., Brosse C.D., Mai S., Truneh A.,Carte B. Novel alkaloids from the sponge batzella sp.: inhibitors of HIV gp120-human CD4binding[J].J. Org. Chem.,1995,60(5),1182-1188.
[144](a) Heravi M.M., Asadi S., Lashkariani B.M. Recent progress in asymmetric Biginelli reaction[J].Mol. Divers.,2013,17(2),389-407;(b) Panda S.S., Khanna P., Khanna L. Biginelli reaction: a green perspective[J]. Curr. Org. Chem.,2012,16(4),507-520.
[145] Biginelli P. Aldehyde-urea derivatives of aceto-and oxaloacetic acids[J]. Gazz. Chim. Ital.,1893,23,360-413.
[146](a) Atwal K.S., Rovnyak G.C., O’Reilly B.C., Schwartz J. Substituted1,4-dihydropyrimidines.3.Selectively functionalized2-hetero1,4-dihydropyrimidines[J]. J. Org. Chem.,1989,54(25),5898-5907;(b) Barluenga J., Tomas M., Ballesteros A., Lopez L.A.1,4-Cycloaddition of1,3-diazabutadieneswith enamines: an efficient route to the pyrimidine ring[J]. Tetrahedron Lett.,1989,30(34),4573-4576.
[147](a) Kalita H.R., Phukan P. CuI as reusable catalyst for the Biginelli reaction[J]. Catal. Commun.,2007,8(2),179-182;(b) Suzuki I., Suzumura Y., Takeda K. Metal triflimide as a Lewis acid catalyst for Biginelli reactionsin water[J]. Tetrahedron Lett.,2006,47(45),7861-7864;(c) Ma Y., Qian C., Wang L., Yang M. Lanthanide triflate catalyzed Biginelli reaction. One-potsynthesis of dihydropyrimidinones under solvent-free conditions[J]. J. Org. Chem.,2000,65(12),3864-3868;(d) Bose D.S., Fatima L., Mereyala H.B. Green chemistry approaches to the synthesis of5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-potcondensation reaction: comparison of ethanol, water, and solvent-free conditions[J]. J. Org. Chem.,2003,68(2),587-590;(e) Shaabani A., Bazgir A., Teimouri F. Ammonium chloride-catalyzed one-pot synthesis of3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions[J]. Tetrahedron Lett.,2003,44(4),857-859;(f) Reddy Y.T., Rajitha B., Reddy P.N., Kumar B.S., Rao V.P. Bismuth subnitrate catalyzed efficientsynthesis of3,4-dihydropyrimidin-2(1H)-ones: an improved protocol for the Biginelli reaction[J].Synth. Commun.,2004,34(20),3821-3825;(g) Fu N.Y., Yuan Y.F., Cao Z., Wang S.W., Wang J.T., Peppe C. Indium (III) bromide-catalyzedpreparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction[J].Tetrahedron,2002,58(24),4801-4807;(h) Lu J., Bai Y., Wang Z., Yang B., Ma H. One-pot synthesis of3,4-dihydropyrimidin-2(1H)-onesusing lanthanum chloride as a catalyst[J]. Tetrahedron Lett.,2000,41(47),9075-9078;(i) Hassani Z., Islami M.R., Kalantari M. An efficient one-pot synthesis of octahydroquinazolinonederivatives using catalytic amount of H2SO4in water[J]. Bioorg. Med. Chem., Lett.2006,16(17),4479-4482.
[148] Zumpe F.L., Flü M., Schmitz K., Lender A. Propane phosphonic acid anhydride: a new promoterfor the one-pot Biginelli synthesis of3,4-dihydropyrimidin-2(1H)-ones[J]. Tetrahedron Lett.,2007,48(8),1421-1423.[149](a) Yadav L.D.S., Rai A., Rai V.K., Awasthi C. Chiral ionic liquid-catalyzed Biginelli reaction:stereoselective synthesis of polyfunctionalized perhydropyrimidines[J]. Tetrahedron,2008,64(7),1420-1429;(b) Gholap A.R., Venkatesan K., Daniel T., Lahoti R.J., Srinivasan K.V. Ionic liquid promoted noveland efficient one pot synthesis of3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature underultrasound irradiation[J]. Green Chem.,2004,6(3),147-150.
[150] Agarwal S., Aware U., Patil A., Rohera V., Ghate M., Jain M., Patel P. Silica-gel catalyzed facilesynthesis of3,4-dihydropyrimidinones[J]. Bull. Korean Chem. Soc.,2012,33(2),377-378.
[151] Debache A., Chouguiata L., Boulcinaa R., Carboni B. A one-pot multi-component synthesis ofdihydropyrimidinone/thione and dihydropyridine derivatives via Biginelli and Hantzschcondensations using t-BuOK as a catalyst under solvent-free conditions[J]. Open Org. Chem. J.,2012,6,12-20.
[152](a) Stefani H.A., Gatti P.M.3,4-Dihydropyrimidin-2(1H)-ones: fast synthesis under microwaveirradiation in solvent free conditions[J]. Synth. Commun.,2000,30(12),2165-2173;(b) Yadav J.S., Reddy B.V.S., Reddy E.J., Ramalingam T. Microwave-assisted efficient synthesis ofdihydropyrimidines: improved high yielding protocol for the Biginelli reaction[J]. J. Chem. Res.,2000,(7),354-355;(c) Mirza-Aghayan M., Bolourtchian M., Hosseini M. Microwave-assisted efficient synthesis ofdihydropyrimidines in solvent-free condition[J]. Synth. Commun.,2004,34(18),3335-3341;(d) Stadler A., Kappe C.O. Microwave-mediated Biginelli reactions revisited. On the nature of rateand yield enhancements[J]. J. Chem. Soc., Perkin Trans.2,2000,(7),1363-1368;(e) Reddy C.S., Nagaraj A. Zirconium oxychloride as a new and efficient catalyst for the synthesis of3,4-dihydropyrimidine-2(1H)-thione/one under solvent-free microwave irradiation conditions[J].Heter. Commun.,2007,13(1),67-72.
[153](a) Liu C.J., Wang J.D. Ultrasound-assisted synthesis of novel4-(2-phenyl-1,2,3-triazol-4-yl)-3,4-dihydropyrimidin-(1H)-(thio)ones catalyzed by Sm(ClO4)3[J]. Molecules,2010,15(4),2087-2095;(b) Borik R.M. A comparison on microwave and ultrasound accelerated synthetic route todihydropyrimidinones catalyzed by sulfanilic acid in water[J]. Aust. J. Basic&Appl. Sci.,2013,7(1),543-547;(c) Dutta M., Gogoi J., Shekarrao K., Goswami J., Gogoi S., Boruah R.C. Simple ultrasound-assistedsynthesis of3,4-dihydropyrimidin-2(1H)-one and3,4-dihydropyrimidine-2(1H)-thione-fused steroidalderivatives by a three-component reaction[J]. Synthesis,2012,44(16),2614-2622;(d) Yadav J.S, Reddy B.V.S., Reddy K.B., Raj K.S., Prasad A.R. Ultrasound-accelerated synthesis of3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate[J]. J. Chem. Soc., Perkin Trans.1,2001,(16),1939-1941;(e) Guo S., Yuan Y. One-pot synthesis of1,4-dihydropyridine and polyhydro-quinoline derivatives viaL-proline catalyzed Hantzsch multicomponent reaction under ultrasound irradiation[J]. Chin. J. Chem.,2010,28(5),811-817.
[154] 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 calcium channelmodulators[J]. Tetrahedron Lett.,2012,53(49),6725-6728.
[155] Wang J.S., Li J.T., Lin Z.P. Iodine catalyzed one-pot synthesis of3,4-dihydropyrimidin-2(1H)-onesunder ultrasound irradiation[J]. Lett. Org. Chem.,2006,3(7),523-525.
[156] Bonola G., Sianesi E.2,3-Dihydro-4(1H)-quinazolinone derivatives[J]. J. Med. Chem.,1970,13(2),329-332.
[157](a) Alaimo R.J., Russell H.E. Antibacterial2,3-dihydro-2-(5-nitro-2-thienyl) quinazolin-4-(1H)-ones[J]. J. Med. Chem.,1972,15(3),335-336;(b) Li Q., Mitscher L.A., Shen L.L. The2-pyridone antibacterial agents: bacterial topoisomeraseinhibitors[J]. Med. Res. Rev.,2000,20(4),231-293.
[158](a) Chinigo G.M., Paige M., Grindrod S., Hamel E., Dakshanamurthy S., Chruszcz M., Minor W.,Brown M.L. Asymmetric synthesis of2,3-dihydro-2-arylquinazolin-4-ones: methodology andapplication to a potent fluorescent tubulin inhibitor with anticancer activity[J]. J. Med. Chem.,2008,51(15),4620-4631;(b) Berman E.M., Werbel L.M. The renewed potential for folate antagonists in contemporary cancerchemotherapy[J]. J. Med. Chem.,1991,34(2),479-485;(c) Mohammadi A.A, Dabiri M., Qaraat H. A regioselective three-component reaction for synthesis ofnovel1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives[J]. Tetrahedron,2009,65(18),3804-3808;(d) Liu J., Fu Z., Li A.R., Johnson M., Zhu L., Marcus A., Danao J., Sullivan T., Tonn G., Collins T.,Medina J. Optimization of a series of quinazolinone-derived antagonists of CXCR3[J]. Bioorg. Med.Chem. Lett.,2009,19(17),5114-5118.
[159](a) Cox R.J., O'Hagan D. Synthesis of isotopically labelled3-amino-2-phenylpropionic acid and itsrole as a precursor in the biosynthesis of tenellin and tropic acid[J]. J. Chem. Soc., Perkin Trans.1,1991(10),2537-2540;(b) Bartroli J., Turmo E., Alguero M., Boncompte E., Vericat M.L., Conte L., Ramis J., Merlos M.,Garcia-Rafanell J., Forn J. New azole antifungals.3. Synthesis and antifungal activity of3-substituted-4(3H)-quinazolinones[J]. J. Med. Chem.,1998,41(11),1869-1882.
[160](a) Nagarajan M., Xiao X., Antony S., Kohlhagen G., Pommier Y., Cushman M. Design, synthesis,and biological evaluation of indenoisoquinoline topoisomerase I inhibitors featuring polyamine sidechains on the lactam nitrogen[J]. J. Med. Chem.,2003,46(26),5712-5724;(b) Hasvold L.A., Wang W., Gwaltney S.L., Rockway T.W., Nelson L.T.J., Mantei R.A., FakhouryS.A., Sullivan G.M., Li Q., Lin N.H., Wang L., Zhang H.Y., Cohen J., Gu W.Z., Marsh K., Bauch J.,Rosenberg S., Sham H.L. Pyridone-containing farnesyltransferase inhibitors: synthesis and biologicalevaluation[J]. Bioorg. Med. Chem. Lett.,2003,13(22),4001-4005;(c) Wu H., Xie X., Liu G. Parallel solution phase synthesis of3,6,7-4(3H)-quinazolinones andevaluation of their antitumor activities against human cancer[J]. J. Comb. Chem.,2010,12(3),346-355.
[161] Srivastava V.K., Kumar A. Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents[J]. Eur. J. Med. Chem.,2002,37(11),873-882.
[162] El-Sabbagh O.I., Ibrahim S.M., Baraka M.M., Kothayer H. Synthesis of new2,3-dihydroquinazolin-4(1H)-one derivatives for analgesic and anti-inflammatory evaluation[J]. Arch. Pharm.Chem. Life Sci.,2010,343(5),274-281.
[163](a) Ram V.J., Tripathi B.K., Srivastava A.K. Synthesis and antihyperglycemic activity of suitablyfunctionalized3H-quinazolin-4-ones[J]. Bioorg. Med. Chem.,2003,11(11),2439-2444;(b) Levin J.I., Chan P.S., Bailey T., Katocs A.S., Venkatesan A.M. The synthesis of2,3-dihydro-4(1H)-quinazolinone angiotensin II receptor antagonists[J]. Bioorg. Med. Chem. Lett.,1994,4(9),1141-1146.
[164] Rudolph J., Esler W.P., O'Connor S., Coish P.D.G., Wickens P.L., Brands M., Bierer D.E.,Bloomquist B.T., Bondar G., Chen L., Chuang C.Y., Claus T.H., Fathi Z., Fu W., Khire U.R., KristieJ.A., Liu X.G., Lowe D.B., Mcclure A.C., Michels M., Ortiz A.A., Ramsden P.D., Schoenleber R.W.,Shelekhin T.E., Vakalopoulos A., Tang W.F., Wang L., Yi L., Gardell S.J., Livingston J.N., SweetL.J., and Bullock W.H. Quinazolinone derivatives as orally available ghrelin receptor antagonists forthe treatment of diabetes and obesity[J]. J. Med. Chem.,2007,50(21),5202-5216.
[165](a) Dolle V., Fan E., Nguyen C.H., Aubertin A.M., Kirn A., Andreola M.L., Jamieson G.,Tarrago-Litvak L., Bisagni E. A new series of pyridinone derivatives as potent non-nucleoside humanimmunodeficiency virus type1specific reverse transcriptase inhibitors[J]. J. Med. Chem.,1995,38(23),4679-4686;(b) Wai J.S., Williams T.M., Bamberger D.L., Fisher T.E., Hoffman J.M., Hudcosky R.J., ToughS.C.M., Rooney C.S., Saari W.S. Synthesis and evaluation of2-pyridinone derivatives as specificHIV-1reverse transcriptase inhibitors.3. Pyridyl and phenyl analogs of3-aminopyridin-2(1H)-one[J].J. Med. Chem.,1993,36(2),249-255.
[166] Maskey R.P., Shaaban M., Grün-Wollny I., Laatsch H. Quinazolin-4-one derivatives fromstreptomyces isolates[J]. J. Nat. Prod.,2004,67(7),1131-1134.
[167] Connolly D.J., Cusack D., O'Sullivan T.P., Guiry P.J. Synthesis of quinazolinones andquinazolines[J]. Tetrahedron,2005,61(43),10153-10202.
[168](a) Moore J.A., Sutherland G.J., Sowerby R., Kelly E.G., Palermo S., Webster W. Reactions ofanthranilamide and o-aminoacetophenone with benzil and benzoin[J]. J. Org. Chem.,1969,34(4),887-892;(b) Khurana J.M., Kukreja G. Nickel boride mediated reductive desulfurization of2-thioxo-4(3H)-quinazolinones: A new synthesis of quinazolin-4(3H)-ones and2,3-dihydro-4(1H)-quinazolinones[J].J. Heterocyclic Chem.,2003,40(4),677-679;(c) Sadanandam Y.S., Reddy K.R.M., BhaskarRao A. Synthesis of substituted2,3-dihydro-1-(β-phenylethyl)-2-aryl and2,3-diaryl-4(1H)-quinazolinones and their pharmacological activities[J]. Eur. J.Med. Chem.,1987,22(2),169-173.
[169] Li J.T., Yin Y., Sun M.X. An efficient one-pot synthesis of2,3-epoxyl-1,3-diaryl-1-propanone directlyfrom acetophenones and aromatic aldehydes under ultrasound irradiation[J]. Ultrason. Sonochem.,2010,17(2),363-366.
[170](a) Salehi P., Dabiri M., Zolfigol M.A., Baghbanzadeh M. A novel method for the one-potthree-component synthesis of2,3-dihydroquinazolin-4(1H)-ones[J]. Synlett,2005,2005(7),1155-1157;(b) Dabiri M., Salehi P., Otokesh S., Baghbanzadeh M., Kozehgary G., Mohammadi A.A. Efficientsynthesis of mono-and disubstituted2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2·12H2O as areusable catalyst in water and ethanol[J]. Tetrahedron Lett.,2005,46(36),6123-6126.
[171] Narasimhulu M., Lee Y.R. Ethylenediamine diacetate-catalyzed three-component reaction for thesynthesis of2,3-dihydroquinazolin-4(1H)-ones and their spirooxindole derivatives[J]. Tetrahedron,2011,67(49),9627-9634.
[172] Chen J.X., Wu D.Z., He F., Liu M.C., Wu H.Y., Ding J.C., Su W.K. Gallium (III) triflate-catalyzedone-pot selective synthesis of2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones[J].Tetrahedron Lett.,2008,49(23),3814-3818.
[173] Ghorbani-Choghamarani A., Taghipour T. Green and one-pot three-component synthesis of2,3-dihydroquinazolin-4(1H)-ones promoted by citric acid as recoverable catalyst in water[J]. Lett.Org. Chem.,2011,8(7),470-476.
[174] Niknam K., Jafarpour N., Niknam E. Silica-bonded N-propylsulfamic acid as a recyclable catalyst forthe synthesis of2,3-dihydroquinazolin-4(1H)-ones[J]. Chin. Chem. Lett.,2011,22(1),69-72.
[175] Niknam K., Mohammadizadeh M.R., Mirzaee S. Silica-bonded S-sulfonic acid as a recyclablecatalyst for synthesis of2,3-dihydroquinazolin-4(1H)-ones[J]. Chin. J. Chem.,2011,29(7),1417-1422.
[176] Dabiri M., Salehi P., Baghbanzadeh M., Zolfigol M.A., Agheb M., Heydari S. Silica sulfuric acid: Anefficient reusable heterogeneous catalyst for the synthesis of2,3-dihydroquinazolin-4(1H)-ones inwater and under solvent-free conditions[J]. Catal. Commun.,2008,9(5),785-788.
[177] Wang M., Zhang T.T., Liang Y., Gao J.J. Strontium chloride-catalyzed one-pot synthesis of2,3-dihydroquinazolin-4(1H)-ones in protic media[J]. Chin. Chem. Lett.,2011,22(12),1423-1426.
[178] Rostamizadeh S., Amani A.M., Mahdavinia G.H., Sepehrian H., Ebrahimi S. Synthesis of some novel2-aryl-substituted2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions using MCM-41-SO3H as a highly efficient sulfonic acid[J]. Synthesis,2010,2010(8),1356-1360.
[179] Zhang Z.H., Lü H.Y., Yang S.H., Gao J.W. Synthesis of2,3-dihydroquinazolin-4(1H)-ones bythree-component coupling of isatoic anhydride, amines, and aldehydes catalyzed by magnetic Fe3O4nanoparticles in water[J]. J. Comb. Chem.,2010,12(5),643-646.
[180] Shaterian H.R., Oveisi A.R., Honarmand M. Synthesis of2,3-dihydroquinazoline-4(1H)-ones[J].Synth. Commun.,2010,40(8),1231-1242.
[181] Salehi P., Dabiri M., Baghbanzadeh M., Bahramnejad M. One-pot, three-component synthesis of2,3-dihydro-4(1H)-quinazolinones by Montmorillonite K-10as an efficient and reusable catalyst[J].Synth. Commun.,2006,36(16),2287-2292.
[182] Kassaee M.Z., Rostamizadeh S., Shadjou N., Motamedi E., Esmaeelzadeh M. An efficient one-potsolvent-free synthesis of2,3-dihydroquinazoline-4(1H)-ones via Al/Al2O3nanoparticles[J]. J.Heterocyclic Chem.,2010,47(6),1421-1424.
[183] Rostamizadeh S., Amani A.M., Aryan R., Ghaieni H.R., Shadjou N. Synthesis of new2-arylsubstituted2,3-dihydroquinazoline-4(1H)-ones under solvent-free conditions, using molecular iodineas a mild and efficient catalyst[J]. Synth. Commun.,2008,38(20),3567-3576.
[184] Baghbanzadeh M., Salehi P., Dabiri M., Kozehgary G. Water-accelerated synthesis of novelbis-2,3-dihydroquinazolin-4(1H)-one derivatives[J]. Synthesis,2006,2006(2),344-348.
[185]宋志国,王洋,孙啸虎,刘连利,张婷婷.“一锅法”合成2,3-二氢-4(1H)-喹啉唑酮衍生物[J].石油化工高等学校学报,2011,24(6),46-49.
[186]王敏,张婷婷,梁艳,高晶晶.对甲基苯磺酸亚铈催化一锅法合成取代2,3-二氢-4(1H)-喹唑啉酮[J].化学研究与应用,2012,24(6),980-985.
[187](a) Chen J., Su W., Wu H., Liu M., Jin C. Eco-friendly synthesis of2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid–water without additional catalyst[J]. Green Chem.,2007,9(9),972-975;(b) Darvatkar N.B., Bhilare S.V., Deorukhkar A.R., Raut D.G., Salunkhe M.M.[bmim]HSO4: anefficient and reusable catalyst for one-pot three-component synthesis of2,3-dihydro-4(1H)-quinazolinones[J]. Green Chem. Lett. Rev.,2010,3(4),301-306.
[188]许碧晖,夏盛,荣良策.无溶剂条件下有效合成2,3-二氢-4(1H)-喹唑啉酮衍生物[J].徐州师范大学学报(自然科学版),2011,29(3),62-65.
[189] Surpur M.P., Singh P.R., Patil S.B., Samant S.D. Expeditious one-pot and solvent-free synthesis ofdihydroquinazolin-4(1H)-ones in the presence of microwaves[J]. Synth. Commun.,2007,37(12),1965-1970.
[190] Safari J., Gandomi-Ravandi S. Microwave-accelerated three components cyclocondensation in thesynthesis of2,3-dihydroquinazolin-4(1H)-ones promoted by Cu-CNTs[J]. J. Mol. Catal. A: Chem.,2013,371,135-140.
[191](a) Li C.J., Chan T.H. Organic Reactions in Aqueous Media,2nd ed.[M]. Wiley: Hoboken, NJ,2007;(b) Pirrung M.C. Acceleration of organic reactions through aqueous solvent effects[J]. Chem. Eur. J.,2006,12(5),1312-1317.
[192](a) Li C.J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: adecade update[J]. Chem. Rev.,2005,105(8),3095-3166;(b) Kobayashi S., Manabe K. Development of novel Lewis acid catalysts for selective organicreactions in aqueous media[J]. Acc. Chem. Res.,2002,35(4),209-217;(c) Li J.T., Sun M.X. SiO2·12WO3·24H2O: a highly efficient catalyst for the synthesis of5-arylidenebarbituric acid in the presence of water[J]. Aust. J. Chem.,2009,62(4),353-355;(d) Tan J.N., Li H.Q., Gu Y.L. Water mediated trapping of active methylene intermediates generatedby IBX-induced oxidation of Baylis–Hillman adducts with nucleophiles[J]. Green Chem.,2010,12(10),1772-1782.
[193] Manabe K., Kobayashi S. Mannich-type reactions of aldehydes, amines, and ketones in a colloidaldispersion system created by a Br nsted acid-surfactant-combined catalyst in water[J]. Org. Lett.,1999,1(12),1965-1967.
[194](a) Manabe K., Mori Y., Kobayashi S. Three-component carbon-carbon bond-forming reactionscatalyzed by a Br nsted acid-surfactant-combined catalyst in water[J]. Tetrahedron,2001,57(13),2537-2544;(b) Peng Y.Y, Zhang Q.L., Yuan J.J., Cheng J.P. A facile aqueous synthesis of bis(indol-3-yl) alkanescatalyzed by dodecylbenzenesulfonic acid[J]. Chin. J. Chem.,2008,26(12),2228-2232;(c) Esmaeilpour M., Sardarian A.Z.4-Dodecylbenzenesulfonic acid(DBSA): an efficient, eco-friendlyand chemoselective catalyst for the synthesis of1,1-diacetates under solvent-free conditions at roomtemperature[J]. Iranian J. Sci. Technol.,2013,37(A3),277-284.
[195](a) Li J.T., Sun M.X., He G.Y., Xu X.Y. Efficient and green synthesis of bis(indolyl)methanescatalyzed by ABS in aqueous media under ultrasound irradiation[J]. Ultrason. Sonochem.,2011,18(1),412-414;(b) Li J.T., Li Y.W., Song Y.L. Efficient Synthesis of12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasoundirradiation[J]. Synth. Commun.,2012,42(14),2161-2170;(c) Li J.T., Du C., Xu X.Y., Chen G.F. Synthesis of2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueousmedia under ultrasound irradiation[J]. Ultrason. Sonochem.,2012,19(5),1033-1038.