Microwave-assisted multicomponent reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)-thiones using lanthanum oxide as a catalyst under solvent-free conditions

被引:20
作者
Kuraitheerthakumaran, A. [1 ]
Pazhamalai, S. [1 ]
Gopalakrishnan, M. [1 ]
机构
[1] Annamalai Univ, Dept Chem, Annamalainagar 608002, Tamil Nadu, India
关键词
3,4-Dihydropyrimidinone; Lanthanum oxide; Biginelli reaction; Microwave; Solvent-free; ONE-POT SYNTHESIS; BIGINELLI REACTION; SCANDIUM TRIFLUOROMETHANESULFONATE; REUSABLE CATALYST; ORGANIC-SYNTHESIS; TRIFLATE; ACID; 3,4-DIHYDROPYRIMIDINE-2(1H)-ONES; DIHYDROPYRIMIDINONES; EFFICIENT;
D O I
10.1016/j.arabjc.2011.06.005
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of 3,4-dihydropyrimidinone derivatives using lanthanum oxide as a catalyst, from aldehydes, beta-keto ester and urea/thiourea without solvent under the irradiation of microwave is described. Compared with classical Biginelli reaction conditions, this new method has the advantage of excellent yields and shorter reaction times. (C) 2011 Production and hosting by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码:S461 / S465
页数:5
相关论文
共 22 条
[1]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
KIMBALL, SD ;
FLOYD, DM ;
MORELAND, S ;
SWANSON, BN ;
GOUGOUTAS, JZ ;
SCHWARTZ, J ;
SMILLIE, KM ;
MALLEY, MF .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2629-2635
[2]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[3]   Antimony(III) chloride-catalysed Biginelli reaction: a versatile method for the synthesis of dihydropyrimidinones through a different reaction mechanism [J].
Cepanec, Ivica ;
Litvic, Mladen ;
Filipan-Litvic, Mirela ;
Grungold, Ivana .
TETRAHEDRON, 2007, 63 (48) :11822-11827
[4]   Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction [J].
Chitra, S. ;
Pandiarajan, K. .
TETRAHEDRON LETTERS, 2009, 50 (19) :2222-2224
[5]   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
[6]   12-molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones [J].
Heravi, Majid M. ;
Bakhtiari, Khadijeh ;
Bamoharram, Fatemeh F. .
CATALYSIS COMMUNICATIONS, 2006, 7 (06) :373-376
[7]   Microwave-assisted heterocyclic synthesis [J].
Katritzky, AR ;
Singh, SK .
ARKIVOC, 2003, :68-86
[8]  
KAWADA A, 1994, SYNLETT, P545
[9]  
Kobayashi S, 1999, EUR J ORG CHEM, V1999, P15
[10]  
KOBAYASHI S, 1993, SYNLETT, P472