Особливості взаємодії 5-трифлуорометил-вміснихпохідних 1,2,4-триазол-3-тіону з пропаргіл бромідом

Abstract

Chemistry of 1,2,4-triazole-3-thione derivatives is an area of active scientific investigations today. This is primarily due to the practical value of such compounds It is well known that due to their biological activity, 1,2,4-triazole-3-thione derivatives are successfully used in such fields as pharmacy, agrochemistry and photography. The Department of Organic Chemistry of Uzhhorod National University is known for its active research in the development of new methods for the synthesis of functional derivatives of 1,2,4- triazole-3-thione, as well as in the study of their properties and their strategic modification to increase biological activity and value in general. In this context, one of the modern methods of heterocyclic systems functionalization is the introduction of fluorine-containing substituents. It is known that the substrates obtained in this way are usually characterized by greater lipophilicity and less toxicity compared to non-fluorinated analogues. Having some own developments on the effective introduction of fluorine-containing substituents into the 1,2,4-triazole-3-thione system, it became relevant to study the features of further transformations of obtained fluorine-containing derivatives.In the framework of this study propargyl substitute deserves special attention/. Being a highly nucleophilic alkyl functional moiety with an acidic terminal hydrogen atom, the propargyl substituent is able to influence on the course of a chemical reaction in significant way. The aim of this work is to investigate the interaction of 5-trifluoromethylcontaining 1,2,4- triazol-3-thione derivatives with propargyl bromide. It should be noted that this kind of investigation has not been conducted before. It has been investigated the peculiarities of the reaction of 5-trifluoromethyl-4-phenyl-1,2,4- triazole-3-thione with propargyl bromide in comparison with the corresponding non-fluorinated substrates, selected and tested the conditions for the selective production of 4-phenyl-3- (prop-2-yn-1- ylsulfanyl) -5-trifluoromethyl-4H-1,2,4-triazole 3, and demonstrated the effectiveness of this approach for similar reactions in the example of 4-methyl-3- (prop- 2-yn-1-ylsulfanyl) -5-trifluoromethyl-4H- 1,2,4-triazole 4