Novel one-step method for the conversion of isothiocyanates to 2-alkyl(aryl)aminothiazoles

被引：18
|
作者：
Sasmal, Pradip K. [1 ]
Chandrasekhar, A. [1 ]
Sridhar, S. [1 ]
Iqbal, Javed [1 ]
机构：
[1] Dr Reddys Labs Ltd, Discovery Res, Hyderabad 500049, Andhra Pradesh, India
来源：
TETRAHEDRON | 2008年 / 64卷 / 49期
关键词：
Thiazoles; Intramolecular thia-Michael reaction; Isothiocyanates; Thiazolylmethylphosphonates;
D O I：
10.1016/j.tet.2008.09.074
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Aminothiazole derivatives are widely used structural motifs in medicinal chemistry due to their broad application in drug development. Herein we demonstrate a novel one-step method for the synthesis of 2-aminothiazole derivatives from the corresponding isothiocyanates via thiourea formation followed by cycloisomerisation in an intramolecular thia-Michael fashion. This method is very mild, simple and highly efficient and versatile enough to accommodate various amino substitutions at the C2 position of thiazoles. This methodology is equally well applicable to synthesise various 2-substituted amino-5-thiazolylmethylphosphonate derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：11074 / 11080
页数：7
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