Tangstophosphoric acid (H3PW12O40):: An efficient and eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1H)-ones

被引：94

作者：

Amini, Mostafa Mohammadpour ^{[1
]}

Shaabani, Ahmad ^{[1
]}

Bazgir, Ayoob ^{[1
]}

机构：

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

来源：

CATALYSIS COMMUNICATIONS | 2006年 / 7卷 / 11期

关键词：

heteropolyacid; tangstophosphoric acid; dihydropyrimidinones; Biginelli reaction; solvent-free;

D O I：

10.1016/j.catcom.2006.02.027

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：

Tangstophosphoric acid both in bulk form or supported on silica gel efficiently catalyzed the three-component condensation reaction of aldehyde, 1,3-dicarbonyl compound and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones in high yields under solvent-free conditions at 80 degrees C. This catalyst is efficient not only for open chained beta-dicarbonyl compounds, but for the cyclic beta-diketones, beta-diester or beta-diamide derivatives such as dimedone, Meldrum's acid or barbituric acid derivatives. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：843 / 847

页数：5

共 42 条

[1]

[Anonymous], CATALYSIS FINE CHEM

[2]

ATWAL KS, 1987, HETEROCYCLES, V26, P1189

[3] 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

[4] 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

[5] 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

[6]

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

[7] 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

[8] DIHYDROPYRIMIDINES - NOVEL CALCIUM-ANTAGONISTS WITH POTENT AND LONG-LASTING VASODILATIVE AND ANTIHYPERTENSIVE ACTIVITY [J].

CHO, H ;

UEDA, M ;

SHIMA, K ;

MIZUNO, A ;

HAYASHIMATSU, M ;

OHNAKA, Y ;

TAKEUCHI, Y ;

HAMAGUCHI, M ;

AISAKA, K ;

HIDAKA, T ;

KAWAI, M ;

TAKEDA, M ;

ISHIHARA, T ;

FUNAHASHI, K ;

SATOH, F ;

MORITA, M ;

NOGUCHI, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2399-2406

[9] 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

[10] Improved synthesis and preparative scale resolution of racemic monastrol [J].

Dondoni, A ;

Massi, A ;

Sabbatini, S .

TETRAHEDRON LETTERS, 2002, 43 (34) :5913-5916

← 1 2 3 4 5 →