A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride

被引：126

作者：

Sun, Q ^{[1
]}

Wang, YQ ^{[1
]}

Ge, ZM ^{[1
]}

Cheng, TM ^{[1
]}

Li, RT ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2004年 / 07期

关键词：

Biginelli reaction; dihydropyrimidinones; zinc chloride; solvent-free; catalvst;

D O I：

10.1055/s-2004-822331

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dihydropyrimidinones are prepared from zinc chloride (20 mol%) catalyzed Biginelli condensation of an aldehyde, 1,3-dicarbonyl compounds and urea or thiourea at 80 degreesC for short time under solvent-free conditions in high yields.

引用

页码：1047 / 1051

页数：5

共 36 条

[1]

Aswal K.S., 1990, J MED CHEM, V33, P2629

[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] 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

[4]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[5] 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

[6]

Bruce M.A., 1998, PCT Int. Appl. Chem. Abstr, Patent No. [9833791, 9833,791]

[7] A new substrate for the Biginelli cyclocondensation:: Direct preparation of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones from a β-keto carboxylic acid [J].

Bussolari, JC ;

McDonnell, PA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6777-6779

[8] 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

[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] 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

← 1 2 3 4 →