Synthesis of novel 2-aminothiazole derivatives

Abstract

The aminothiazole ring system is a useful structural element in medicinal chemistry and has found broad application in drug development for the treatment of allergies,1 hypertension,2 inflammation,3 bacterial infection4 and HIV.5 2-Aminothiazoles are usually synthesized by the condensation of α-haloketones with monosubstituted thioureas.6 In view of this important biological activity of thiazole derivatives we have decided to investigate the conventional functionalisation reactions (sulfonylation, condensation) of amino group in different 2-aminothiazoles-carboxylates to gain access to the new potentially biologically active compounds7,8. The condensation reaction of substituted aldehydes with aminothiazole carboxylate give the N-alkylated imines. Sulfonylation of ethyl-2-amino-4-methylthiazole-5-carboxylate and ethyl-2-aminothiazol-4-yl)ethanoate proceseded successfully and were obtained in the same reaction mixture mono- and disulfonated derivatives.