Synthesis of some optically active thiazole derivatives

Abstract

Optically active and racemic 4-s-butylthiazole and 2-amino-4-s-butylthiazole were prepared in 50 and 85% yields, respectively, from s-butyl diazomethyl ketone (prepared from 2-methylbutanoic acid). The optically active heterocyclic compounds were correlated via the Chichibabin reaction and the stereoselectivity of the reactions employed was established by ozonolysis of (+)-(S)-4-s-butylthiazole and (+)-(S)-2-amino-4-s-butylthiazole to (+)-(S)-2-methylbutanoic acid.