Synthesis of series S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonthioates and investigation of their further oxidation
Journal Title: Фармацевтичний журнал - Year 2014, Vol 3, Issue 3
Abstract
hemistry of 1,2,4-triazole attracts both domestic and foreign researchers due to the fact that, based on this heterocycle created substances widely used in various spheres of life . Widely studied synthetic, physical-chemical and biological properties of 1,2,4-triazole-3-thione with various substituents on the heterocyclic structure as well as the sulfur atom but there is no information about studying the reactions of obtaining a series of S-5R-4-R1-4H-1,2,4-triazole-3-ilsulfonthioats and study their further oxidation, which was the goal of our research. It was studied several acylation reactions previously obtained 5-R-4-R1-1,2,4-triazole-3-thiones, using benzenesulfonylchloride as the acylating agent, 4-toluenesulfonyl chloride and metiluratsilsulfohloridafor solution this goal. This reaction has been carried out at room temperature. 5-R-4-R1-1,2,4-triazole-3-thione derivatives have been heated with an equivalent amount of hydroxide and the sulfonyl chlorides was addedas 1,4-dioxane solution (benzensulfonyl, 4-toluensulfonyl chloride), or in crystalline form (using methyluracilsulfchloride) only after cooling the reaction mixture. Substances from S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonthyoateshave been oxidized to 5-R-4-R1-3-ilsulfonil-4H-1,2,4-triazole in order to expand the range of pharmacologically active substances. Oxidation reaction has been carried out with pergydrole in a concentrate acetate acid. The structure of the obtained S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonothyoatshas been identified by elemental analysis and by infrared spectrophotometry. It was used MS-analysis for confirming the structure of the synthesized substances. Thus, the mass spectrum of S-(5-(4-nitrophenil)-4-phenil-4H-1,2,4-triazol-3-il)benzensulfonothyiate (gross formula C20H14N4O4S2 mol. weight 438 a. m. u.) showed peak M+ with m/z 439. Fragmentation of substance proceedswith detachment ofsulfophenyl fragment and with formation of ion with m/z 297-298. Additionally, it was found SO2-fragment (m/z 64) benzene debris (m/z 77) in mass-spectrum of research compound. The structure of the obtained 5-R-4-R1-3-R1-ilsulfonilsulfonil-4H-1,2,4-triazole confirmed by elemental analysis and by IR-spectrophotometry. It was synthesized 15 new compounds derivatives of 1,2,4-triazole-3-thione, which will become the basis for the study of biological activity.
Authors and Affiliations
A. G. Kaplaushenko
Keywords
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