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

被引：270

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.

引用

页码：857 / 859

页数：3

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
ATWAL, KS
ROVNYAK, GC
OREILLY, BC
SCHWARTZ, J
[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
Bigi, F
Carloni, S
Frullanti, B
Maggi, R
Sartori, G
[J]. 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
Bussolari, JC
McDonnell, PA
[J]. 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
Dondoni, A
Massi, A
[J]. 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
Folkers, K
Harwood, HJ
Johnson, TB
[J]. 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
Fu, NY
Yuan, YF
Cao, Z
Wang, SW
Wang, JT
Peppe, C
[J]. 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
Hu, EH
Sidler, DR
Dolling, UH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) : 3454 - 3457
[10] KAPPE CO, 1993, TETRAHEDRON, V49, P6937

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