DMAP-promoted cascade C-S/C-N bonds formation approach to 1,3-thiazolidin-4-ones via annulation of β-ketothioamides with α-halocarboxylic acids at room temperature

被引：16

作者：

Verma, Girijesh Kumar ^{[1
]}

Shukla, Gaurav ^{[1
]}

Nagaraju, Anugula ^{[1
]}

Srivastava, Abhijeet ^{[1
]}

Singh, Maya Shankar ^{[1
]}

机构：

[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India

来源：

TETRAHEDRON | 2014年 / 70卷 / 39期

关键词：

Thiazolidin-4-ones; beta-Ketothioamides; alpha-Halocarboxylic acids; One-pot annulation; DCC; DMAP; FUNCTIONALIZED N; S-KETENE ACETAL; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITIES; EFFICIENT; DERIVATIVES; ACCESS; CONSTRUCTION; REACTIVITY; CHEMISTRY;

D O I：

10.1016/j.tet.2014.07.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple and efficient one-pot straightforward method for the construction of 1,3-thiazolidin-4-ones has been developed by cyclocondensation of beta-ketothioamides and an in situ generated acid anhydride from alpha-halocarboxylic acid in the presence of DCC at room temperature. The attractive features of this strategy include metal-free mild reaction conditions, short reaction time, and efficacy of forming consecutive C-S and C-N bonds and one ring in a single synthetic operation. Noteworthy, a Z-stereochemistry was observed for the exocyclic alpha-oxoketene moiety at 2-position of 1,3-thiazolidine ring. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6980 / 6984

页数：5

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