Issue 10, 1999

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

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 1363-1368

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

C. Boga, L. Forlani, C. Silvestroni, A. Bonamartini Corradi and P. Sgarabotto, J. Chem. Soc., Perkin Trans. 1, 1999, 1363 DOI: 10.1039/A809086F

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