One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid

Dedicated to Prof. W. Bruce Kover on the occasion of his 80^th anniversary

Abstract

A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced the corresponding 2-aminothiazoles in up to 87% yield. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process.

Key words

heterocycles - condensation - thiazole - quinoxaline - green chemistry - tribromoisocyanuric acid - pot-ecomomy - thiourea

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