Ammonium chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions

被引：273

作者：

Shaabani, A ^{[1
]}

Bazgir, A ^{[1
]}

Teimouri, F ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Dept Chem, Tehran, Iran

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 04期

关键词：

Biginelli reaction; dihydropyrimidinones; ammonium chloride; one-pot condensation; solvent-free;

D O I：

10.1016/S0040-4039(02)02612-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ammonium chloride as a very inexpensive and readily available reagent, and efficiently catalyzes one-pot, three component, Biginelli condensation reactions of aldehydes, 1,3-dicarbonyl compounds and urea or thiourea under solvent-free conditions to afford the corresponding 3,4-dihydropyrimidin-2-(1H)-ones in high yields at 100degreesC. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：857 / 859

页数：3

相关论文

共 25 条

[1]

ATWAL KS, 1987, HETEROCYCLES, V26, P1189

[2] 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

[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] 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

[5] 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

[6]

Eynde J. J. V., 1997, HETEROCYCLES, V45, P1967

[7] Researches on pyrimidines CXXX Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines [J].

Folkers, K ;

Harwood, HJ ;

Johnson, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 :3751-3758

[8] 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

[9] Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones [J].

Hu, EH ;

Sidler, DR ;

Dolling, UH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3454-3457

[10]

KAPPE CO, 1993, TETRAHEDRON, V49, P6937