Synthesis of series S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonthioates and investigation of their further oxidation

  • A. G. Kaplaushenko Zaporozhzhia State Medical University
Keywords: 1,2,4-triazoles, acylation, oxidation

Abstract

Chemistry 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.

References

1. Ivanov VP The Chemistry of Heterocyclic Compounds. - M .: Vyssh. school., 1978. - 559 p.

2. Kazitsina L. A. Application of UV, IR, NMR and MASS spectroscopy in organic chemistry. 2 ed., Pererab. and add - Moscow: Izv. Mosk. Un ta, 1979. - 236 p.

3. Kaplaushenko AG Methods of synthesis and biological activity of 1,2,4-triazole-3-thione // Ukr. biopharmac. journ - 2009. - No. 4 (4). - C. 48-56.

4. Kaplushenko A. G., Knysh Y. G., Panasenko O. I. Search of biologically active substances among 4-mono and 4,5-disubstituted 1,2,4-triazole-3-thions and their S-derivatives / / Pharmacist a magazine - 2007. - No. 1. - P. 32-35.

5. Knysh E. G. Synthesis, physical, chemical and biological properties of N- and S-substituted 1,2,4-triazole: Dis. ... Dr. farm. sciences - Kharkiv, 1987. - 350 p.

6. Mohamed Baha'a G., Abdel-Alim Abdel-Alim M., Hussein Mostafa A. Synthesis of 1-acyl-2-alkylothio-1,2,4-triazolobenzimidazoles with antifungal, anti-inflammatoryandanalgesieseffects // Actapharm. - 2006. - Vol. 56, No. 1. - P. 31-48.

7. Nigade G., Chavan P., Deodhar M. Synthesis andanalgesicactivity of new pyridine-based heterocyclic derivatives // Med. Chem Res - 2010. - V. 142. - P. 146-149.
Published
2019-02-12
How to Cite
Kaplaushenko, A. G. (2019). Synthesis of series S-5-R-4-R1-4H-1,2,4-triazol-3-ilsulfonthioates and investigation of their further oxidation. Farmatsevtychnyi Zhurnal, (3), 42-49. Retrieved from https://pharmj.org.ua/index.php/journal/article/view/287
Section
Synthesis and analysis of biologically active compounds