Abstract
2-Mercapto-5(4)-methylimidazole-4(5)-carboxanilide (2), was prepared directly by the reaction of α-aminoacetoacetanilide (1) with ammonium thiocyanate in acetic acid containing a catalytic amount of hydrochloric acid. Alkylation of 2 with alkyl halides or proper α-haloketones led to the formation of the corresponding 2-substituted alkylthio derivatives (3a–e). Cyclization of 3c–e by boiling with acetic anhydride in pyridine or by heating with polyphosphoric acid, led to the formation of 2-(un)substituted-3-substituted-6-methylimidazo[2,1-b]thiazole-5-carboxanilides (4a–c). These synthesized compounds were characterized by EL-MS, NMR spectroscopy and by chemical evidences (compounds were prepared by direct and step-wise methods).
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Faty, R.M., Gaafar, A.M. & Youssef, A.M.S. Selective cyclization of S-substituted imidazolethione: synthesis of polysubstituted imidazothiazoles. J IRAN CHEM SOC 12, 1509–1519 (2015). https://doi.org/10.1007/s13738-015-0621-0
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DOI: https://doi.org/10.1007/s13738-015-0621-0