Green protocol for the Biginelli three-component reaction:: Ag3PW12O40 as a novel, water-tolerant heteropolyacid for the synthesis of 3,4-dihydropyrimidinones

被引:131
作者
Yadav, JS [1 ]
Reddy, BVS [1 ]
Sridhar, P [1 ]
Reddy, JSS [1 ]
Nagaiah, K [1 ]
Lingaiah, N [1 ]
Saiprasad, PS [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Catalysis Div, Hyderabad 500007, Andhra Pradesh, India
关键词
heteropolyacid; multicomponent reactions; polyoxometalates; water media;
D O I
10.1002/ejoc.200300559
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Biginelli three-component condensation of an aldehyde, beta-keto ester, and urea proceeds smoothly on the surface of the silver salt of heteropolyacid (HPA), i.e. Ag3PW12O40, in water to afford the corresponding 3,4-dihydropyrimidinones in high-to-quantitative yields under mild conditions. The heterogeneous solid acid provides ease of separation of the catalyst and isolation of the products. The recovered catalyst can be recycled in subsequent reactions with consistent activity. Compared to the classical Biginelli reaction conditions, this new method has the advantages of improved yields, reusability of the catalyst, an eco-friendly solvent, ease of isolation of products, and simplicity in the experimental procedure. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:552 / 557
页数:6
相关论文
共 38 条
[1]  
ATWAL KS, 1987, HETEROCYCLES, V26, P1189
[2]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].
ATWAL, KS ;
SWANSON, BN ;
UNGER, SE ;
FLOYD, DM ;
MORELAND, S ;
HEDBERG, A ;
OREILLY, BC .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811
[3]   SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
OREILLY, BC ;
SCHWARTZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907
[4]   A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].
Bigi, F ;
Carloni, S ;
Frullanti, B ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468
[5]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[6]   Microwave assisted solvent-free synthesis of dihydropyrimidinones by Biginelli reaction over Si-MCM-41 supported FeCl3 catalyst [J].
Choudhary, VR ;
Tillu, VH ;
Narkhede, VS ;
Borate, HB ;
Wakharkar, RD .
CATALYSIS COMMUNICATIONS, 2003, 4 (09) :449-453
[7]   Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component biginelli and hantzsch cyclocondensations [J].
Dondoni, A ;
Massi, A ;
Minghini, E ;
Sabbatini, S ;
Bertolasi, V .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6172-6183
[8]   Three-component Biginelli cyclocondensation reaction using C-glycosylated substrates.: Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues [J].
Dondoni, A ;
Massi, A ;
Sabbatini, S ;
Bertolasi, V .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6979-6994
[9]   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].
Dondoni, A ;
Massi, A .
TETRAHEDRON LETTERS, 2001, 42 (45) :7975-7978
[10]   Hydrogenation of cyclic ureides under elevated temperatures and pressures I 2-keto-1,21314-tetrahydropyrimidines [J].
Folkers, K ;
Johnson, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :1180-1185