p-Sulfonic acid calixarenes as efficient and reusable organocatalysts for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/-thiones

被引：89

作者：

da Silva, Daniel L. ^{[1
]}

Fernandes, Sergio A. ^{[2
]}

Sabino, Adao A. ^{[1
]}

de Fatima, Angelo ^{[1
]}

机构：

[1] Univ Fed Minas Gerais, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil

[2] Univ Fed Vicosa, Dept Quim, BR-36570000 Vicosa, MG, Brazil

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 48期

关键词：

Calixarene; p-Sulfonic acid calix[4]arene; Organocatalysis; Biginelli reaction; 3,4-Dihydropyrimidin-2(1H)-one; 3,4-Dihydropyrimidin-2(1H)-thione; ONE-POT SYNTHESIS; WATER-SOLUBLE CALIXARENES; PHASE-TRANSFER CATALYSTS; BIGINELLI REACTION; HIGHLY EFFICIENT; BASE PROPERTIES; BRONSTED ACID; SOLVENT; DIHYDROPYRIMIDINONES; CONDENSATION;

D O I：

10.1016/j.tetlet.2011.08.175

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient methodology is proposed for obtaining 3,4-dihydropyrimidin-2(1H)-ones/-thiones through Biginelli reactions. It is based on the use of less than the stoichiometric amount of p-sulfonic acid calixarenes as organocatalysts. A number of aromatic aldehydes as well as urea or thiourea can be employed for successfully synthesizing the corresponding Biginelli adducts. The described methodology is devoid of metal-containing catalysts, which in turn is very attractive for safely producing 3,4-dihydropyrimidin-2-(1H)-ones/-thiones of pharmacological interest. In addition, the catalyst efficiency is not compromised after its successive use in reactions. This is the first report about the application of calixarenes as catalysts in the multicomponent Biginelli reaction. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6328 / 6330

页数：3

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