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

[31] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .4. BASIC 3-SUBSTITUTED-4-ARYL-1,4-DIHYDROPYRIMIDINE-5-CARBOXYLIC ACID-ESTERS - POTENT ANTIHYPERTENSIVE AGENTS [J].

ROVNYAK, GC ;

ATWAL, KS ;

HEDBERG, A ;

KIMBALL, SD ;

MORELAND, S ;

GOUGOUTAS, JZ ;

OREILLY, BC ;

SCHWARTZ, J ;

MALLEY, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (17) :3254-3263

[32] CALCIUM-ENTRY BLOCKERS AND ACTIVATORS - CONFORMATIONAL AND STRUCTURAL DETERMINANTS OF DIHYDROPYRIMIDINE CALCIUM-CHANNEL MODULATORS [J].

ROVNYAK, GC ;

KIMBALL, SD ;

BEYER, B ;

CUCINOTTA, G ;

DIMARCO, JD ;

GOUGOUTAS, J ;

HEDBERG, A ;

MALLEY, M ;

MCCARTHY, JP ;

ZHANG, RA ;

MORELAND, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) :119-129

[33] Vanadium(III) chloride catalyzed Biginelli condensation:: solution phase library generation of dihydropyrimidin-(2H)-ones [J].

Sabitha, G ;

Reddy, GSKK ;

Reddy, KB ;

Yadav, JS .

TETRAHEDRON LETTERS, 2003, 44 (34) :6497-6499

[34] Silica sulfuric acid:: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].

Salehi, P ;

Dabiri, M ;

Zolfigol, MA ;

Fard, MAB .

TETRAHEDRON LETTERS, 2003, 44 (14) :2889-2891

[35] Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions [J].

Shaabani, A ;

Bazgir, A .

TETRAHEDRON LETTERS, 2004, 45 (12) :2575-2577

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

Shaabani, A ;

Bazgir, A ;

Teimouri, F .

TETRAHEDRON LETTERS, 2003, 44 (04) :857-859

[37] A reexamination of Biginelli-like multicomponent condensation reaction: One-pot regioselective synthesis of spiro heterobicyclic rings [J].

Shaabani, Ahmad ;

Bazgir, Ayoob ;

Bijanzadeh, Hamid Reza .

MOLECULAR DIVERSITY, 2004, 8 (02) :141-145

[38] Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D [J].

Snider, BB ;

Chen, JS ;

Patil, AD ;

Freyer, AJ .

TETRAHEDRON LETTERS, 1996, 37 (39) :6977-6980

[39] 3,4-dihydropyrimidin-2(1H)-ones: Fast synthesis under microwave irradiation in solvent free conditions [J].

Stefani, HA ;

Gatti, PM .

SYNTHETIC COMMUNICATIONS, 2000, 30 (12) :2165-2173

[40] Green protocol for the Biginelli three-component reaction:: Ag3PW12O40 as a novel, water-tolerant heteropolyacid for the synthesis of 3,4-dihydropyrimidinones [J].

Yadav, JS ;

Reddy, BVS ;

Sridhar, P ;

Reddy, JSS ;

Nagaiah, K ;

Lingaiah, N ;

Saiprasad, PS .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) :552-557

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