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

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

“…[91] Thiazino[3,4-b][1,2,4]triazolium salts 41 were obtained by the interaction of 1-(perfluoroheptanoyl) thiosemicarbazide and 5-(perfluorohexyl)triazole-3-thiol with methyl phenylpropanoate in boiling acetic acid or ethanol or through halogenation of unsaturated thioderivatives of 5-trifluoromethyl-1,2,4-triazole-3-thiol (Scheme 30). [83,93] In the 1H NMR spectrum of triazolothiazines 41, the SCH 2 protons of the thiazine ring were revealed as nonequivalent one-proton doublets of doublets at 3.61 to 3.67 ppm. The mass-spectrum of 41 showed an expected molecular ion peak at m/z = 335, as well as two ion peaks at m/z = 207.…”

Bioactive Thiazine and Benzothiazine Derivatives: Green Synthesis Methods and Their Medicinal Importance

“…Il’inykh and coworkers made S -alkenyl forms of 5-(trifluoromethyl)-4 H -1,2,4-triazole-3-thiol compounds by treating various alkenyl halides with 2,4-triazoles conjugated with trifluoromethyl and thiol groups [25]. Furthermore the chemical process between the S -alkenyl derivatives and iodine molecules occurs regiospecifically producing new fused halogenated (1,2,4)triazole(3,4- b )(1,3)thiazine compounds (Scheme 11) [25].…”

“…Il’inykh and coworkers made S -alkenyl forms of 5-(trifluoromethyl)-4 H -1,2,4-triazole-3-thiol compounds by treating various alkenyl halides with 2,4-triazoles conjugated with trifluoromethyl and thiol groups [25]. Furthermore the chemical process between the S -alkenyl derivatives and iodine molecules occurs regiospecifically producing new fused halogenated (1,2,4)triazole(3,4- b )(1,3)thiazine compounds (Scheme 11) [25]. The chemical structures of these products were confirmed by elemental analysis, IR and mass spectroscopy and different isotopic ( 1 H-, 13 C- and 19 F-) NMR spectroscopies, including state of the art 2D 1 H- 13 C-HSQC, 1 H- 1 H-COSY, 1 H- 13 C-HMBC correlations, and also by single-crystal XRD technique for better results [25].…”

2-Mercaptoimidazolium halides: structural diversity, stability and spontaneous racemisation

“…26 Despite of the fact that imidazo-, triazolo-or tetrazolothiazines and thiazinium salts are currently extensively researched, [26][27][28][29][30] only a few crystal structures have been reported in the literature. [31][32][33][34][35] Besides their biological properties, thiazine compounds are also key intermediates for thiiranes due to their ability to undergo recyclisation reactions. 36,37 Fig.…”