Journal of the Chemical Society, Perkin Transactions 1

Condensation of thiourea derivatives with carbonyl compounds: one-pot synthesis of N-alkyl-1, 3-thiazol-2-amines and of 3-alkyl-1, 3-thiazolimines

AB Corradi

Index: Boga, Carla; Forlani, Luciano; Silvestroni, Cristian; Corradi, Anna Bonamartini; Sgarabotto, Paolo Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 10 p. 1363 - 1368

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Citation Number: 34

Abstract

The reactions of ketones and N-substituted thioureas, in the presence of HCl (or HBr) and DMSO afford mixtures of the title compounds which are easily separated on a silica gel column. This method avoids the classical use of α-haloketones. The mechanism of these reactions involves the enolization of ketones and the activation of thiourea sulfur, probably by oxygen transfer from DMSO.

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