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

Vitor S. C. de Andrade, Marcio C. S. de Mattos*

*Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, Rio de Janeiro 219745-970, Brazil, Email: mmattosiq.ufrj.br

V. S. C. de Andrade, M. C. S. de Mattos, Synthesis, 2018, 50, 4867-4874.

DOI: 10.1055/s-0037-1610243 (free Supporting Information)


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Abstract

The use of tribromoisocyanuric acid enables a simple and efficient one-pot protocol for the synthesis of 2-aminothiazoles from readily available β-keto esters via α-monohalogenation in aqueous medium and a subsequent reaction with thiourea and DABCO. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively.

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Key Words

heterocycles, condensation, thiazoles, tribromoisocyanuric acid, thioureas, green chemistry, pot-ecomomy,


ID: J66-Y2018