Synthesis of novel fluorine- and iodine-containing [1,2,4]triazolo[3,4-b] [1,3]thiazines based 3-(alkenylthio)-5-(trifluoromethyl)-4H-1,2,4-triazole-3- thiols

Abstract

In this paper we report the synthesis of novel S-alkenyl derivatives of 5-(trifluoromethyl)-4H-1,2,4-triazole-3-thiol via alkenation reaction with different alkenyl halides. Reaction between the resulting S-alkenation products and iodine proceeds regiospecifically to give new fused fluorine- and iodine-containing [1,2,4]triazolo[3,4-b][1,3]thiazine heterocyclic systems. The structure of synthesized compounds was confirmed by mass spectra, IR, 1H, 13C and 19F NMR spectroscopy including 2D 1H-13C HSQC, 1H-1H COSY, 1H-13C HMBC correlations, elemental analysis and single-crystal X-ray diffraction study. © 2013 Elsevier B.V.