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 alpha-haloketones. The mechanism of these reactions involves the enolization of ketones and the activation of thiourea sulfur, probably by oxygen transfer from DMSO.
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 / Boga, C; Forlani, L; Silvestroni, C; Corradi, Anna; Sgarabotto, P.. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - STAMPA. - 1:(1999), pp. 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
CORRADI, Anna;
1999
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 alpha-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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