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Paper | Regular issue | Vol 63, No. 2, 2004, pp.259-270
Published online, 21st November, 2003
DOI: 10.3987/COM-03-9910
Synthesis and Structural Studies of 3-Acylamino-4-amino-2,3-dihydro-2-iminothiazole-5-carboxylates and 4-Acylhydrazino-2-aminothiazole-5-carboxylates

Maria Teresa Cocco,* Cenzo Congiu, Valentina Onnis, and Sandra Ianelli

*Department of Toxicology, University of Cagliari, Via Ospedale 72, I-09124 Cagliari, Italy

Abstract

The preparation of thiazole derivatives through reactions of ethyl 3-amino-3-acylhydrazinopropenoates (1) with inorganic thiocyanates and thiourea was investigated. The reaction of 1 with sodium thiocyanate, in acetic acid in the presence of bromine, afforded ethyl 3-acylamino-4-amino-2,3-dihydro- 2-iminothiazole-5-carboxylates (3) selectively. On reacting the same compounds (1) with thiourea, in acetic acid and in the presence of bromine, 4-acylhydrazino-2-aminothiazole-5-carboxylates (4) were yielded. The structure of the representative compound (3c), ethyl 4-amino-3-benzoyl- amino-2,3-dihydro-2-iminothiazole-5-carboxylate has been solved by means of X-Ray crystallographic data analysis.