One-pot synthesis of dihydropyrimidones using silica-supported heteropoly acid as an efficient and reusable catalyst: Improved protocol conditions for the Biginelli reaction

被引:96
作者
Rafiee, E [1 ]
Shahbazi, F [1 ]
机构
[1] Razi Univ, Fac Sci, Dept Chem, Kermanshah 67149, Iran
关键词
heterogeneous catalysts; dihydropyrimidinones or thiones (DHPMs); supported heteropoly acid; Biginelli reaction; multi component reactions (MCR);
D O I
10.1016/j.molcata.2006.01.049
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient synthesis of 3,4-dihydropyrimidinones or thiones (DHPMs) is described, using silica-supported heteropoly acid H3PW12O40/SiO2 (PW/SiO2) for the first time as the catalyst from an aldehyde, beta-keto ester and urea or thiourea in acetonitrile. Compared to the classical Biginelli reaction conditions, this method consistently has the advantage of excellent yields, mild reaction conditions, ease of workup, survival of different functional groups, and short reaction times. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:57 / 61
页数:5
相关论文
共 58 条
[1]   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
[2]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[3]   New protocol for Biginelli reaction-a practical synthesis of Monastrol [J].
Bose, DS ;
Sudharshan, M ;
Chavhan, SW .
ARKIVOC, 2005, :228-236
[4]   Green chemistry approaches 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].
Bose, DS ;
Fatima, L ;
Mereyala, HB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590
[5]  
Bruce M.A., 1998, PCT Int. Appl. Chem. Abstr, Patent No. [9833791, 9833,791]
[6]   Improved synthesis and preparative scale resolution of racemic monastrol [J].
Dondoni, A ;
Massi, A ;
Sabbatini, S .
TETRAHEDRON LETTERS, 2002, 43 (34) :5913-5916
[7]   HETEROPOLYACIDS SUPPORTED ON ACTIVATED CARBON AS CATALYSTS FOR THE ESTERIFICATION OF ACRYLIC-ACID BY BUTANOL [J].
DUPONT, P ;
VEDRINE, JC ;
PAUMARD, E ;
HECQUET, G ;
LEFEBVRE, F .
APPLIED CATALYSIS A-GENERAL, 1995, 129 (02) :217-227
[8]   Heteropoly acids, their salts and polyoxometalates as heterogenous, efficient and eco-friendly catalysts in organic reactions: Some recent advances [J].
Firouzabadi, H. ;
Jafari, A. A. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2005, 2 (02) :85-114
[9]   Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction [J].
Fu, NY ;
Yuan, YF ;
Cao, Z ;
Wang, SW ;
Wang, JT ;
Peppe, C .
TETRAHEDRON, 2002, 58 (24) :4801-4807
[10]  
Hagen J., 1999, IND CATALYSIS PRACTI