Onysko M. Electrophilic heterocyclization of alkenyl- and alkynyl-functionalized azines in a synthesis of polynuclear heterocyclic systems

The thesis is devoted to the development of a strategy for design of polynuclear heterocyclic systems based on azines; the elucidation of the regularities of electrophilic heterocyclization reactions of alkenyl (alkynyl) -functionalized azines under the action of halogens, chalcogentetrahalides and aryltellurium trihalides; the development of convenient methods for construction of azolo (azino) annelated azines and the research of their chemical and biological properties. It is established the regularities of annelation of an additional nitrogen-containing heterocycle to the azine or diazine backbone in the electrophilic heterocyclization reaction under the action of halogens, depending on the presence and nature of the substituent in the allyl fragment of alkenyl derivatives of azines, the position of the alkenyl substituent. It is elucidated the regiochemistry of the process of electrophilic cyclization of alkenyl (alkynyl) -functionalized azines under the action of chalcogentetrahalides, which depends on the nature of the base azine, the type and position of the alkenyl substituent, the nature of the chalcogen of electrophilic reagent, solvent and reaction conditions. It is detected that tellurium-induced cyclization of N-alkenyl 2(6) -thioxodiazines by p-alkoxyphenyltellurium trichlorides regioselectively forms linearly condensed thiazoline-containing heterocycles of the pyrimidine series. It is found the regularities of electrophilic intramolecular cyclization of 2-S-alkenyl pyrimidin-4-ones under the action of p-alkoxyphenyltellurium trichlorides and it is proved that the direction of heterocyclization depends on the presence of a substituent in position 3 of the pyrimidine cycle. High antibacterial, antifungal and antiplasmolytic activity of tellurium-functionalized polynuclear azines was revealed.