Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction

被引：89

作者：

Starcevich, Jacob T. ^{[1
]}

Laughlin, Thomas J. ^{[1
]}

Mohan, Ram S. ^{[1
]}

机构：

[1] Illinois Wesleyan Univ, Lab Environm Friendly Organ Synth, Dept Chem, Bloomington, IL 61701 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 08期

关键词：

Acetals; Aldehydes; Biginelli reaction; 3,4-Dihydropyrimidin-2(1H)-ones/thiones; Green chemistry; Iron(III) tosylate; Multi-component reactions; ONE-POT SYNTHESIS; SOLVENT-FREE SYNTHESIS; REUSABLE CATALYST; 1,3-DICARBONYL COMPOUNDS; EFFICIENT SYNTHESIS; DIHYDROPYRIMIDINONES; CHLORIDE; ACID; CONDENSATION; ETHERS;

D O I：

10.1016/j.tetlet.2012.12.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of dihydropyrimidinones and dihydropyrimidine thiones has attracted interest due to their biological activities. A common method for their synthesis is the Biginelli reaction, which is a one-pot condensation of an aryl aldehyde, urea (or thiourea), and ethyl acetoacetate. The Biginelli reaction is typically catalyzed by a Bronsted or Lewis acid. However, many of these catalysts such as BF3 center dot Et2O and AlCl3 are corrosive and/or toxic. Our continued interest in environmentally friendly organic synthesis prompted us to investigate the utility of iron(III) tosylate as a catalyst for the Biginelli reaction. The use of acetals in the Biginelli reaction is also reported. Iron(III) tosylate is an attractive catalyst for the Biginelli reaction because of its low cost, low toxicity, and ease of handling. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：983 / 985

页数：3

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