Study of compounds of the 1,2,4-triazole class is relevant in view of the constant increase of areas of their practical use. Derivatives of symmetric triazole are used in medicine, as they exhibit a wide range of physiological activity, as well as in photographic studies, agriculture, industry and as analytical reagents for the determination of heavy metals. Among the great variety of synthetic technologies, the method of electrophilic heterocycling demonstrates the simplicity of implementation, efficiency and versatility for the creation of additional heterocycles of different nature. The classical moving of the cycle annelation according to the electrophilic cyclization method is accompanying by the additional introduction of electrophile moiety as functional group. It makes the yielded products more perspective in a plane of the further investigation of their chemical, physical and biological properties.
The dissertation deals with the development of scientific principles for the use of electrophilic heterocyclysis in the region (stereo) selective construction of condensed derivatives of 1,2,4-triazole; the study of chemical and physicochemical properties of synthesized compounds. A series of S-alkenyl-alkynyl substituted substituted 1,2,4-triazole-3-thiones was synthesized.
To achieve this goal, it was supposed to solve the following tasks: (a) to synthesize the model output compounds - unsaturated thioeters of 3-mercapto-1,2,4-triazoles; (b) investigate the reaction of electrophilic reagents - bromine, iodine, iodine bromide, selenium tetral halides and tellurium - with unsaturated derivatives of 1,2,4-triazole-3-thiol; (c) to study the chemical, chemical, physical and biological properties of the condensed and functional derivatives of the symmetric triazole; (d) establish the structure of the products obtained and evaluate the possible prospects for their use.
A series of S-alkenyl-alkynyl substituted substituted 1,2,4-triazole-3-thiones was synthesized. The reactions of their halogenation and chalcogen halogenation have been investigated, and a number of condensed derivatives of thiazolo[3,2-b][1,2,4] riazoles and thiazino[5,1-b][1,2,4]triazoles have been obtained. The factors that determine the regio- (stereo-)selectivity of the process of electrophilic heterocyclization are determined, depending on the nature of the alkenyl (alkynyl) substituent at the exocyclic sulfur atom. The reactivity of the obtained thiazolo[3,2-b][1,2,4]triazolium condensed salts was investigated. The biological effect of the compounds obtained on pathogenic microorganisms was investigated. Leading compounds with the highest bactericidal and fungicidal activity were found.
