Chebanov V. Multicomponent heterocyclization reactions of carbonyls with polynucleophiles

Investigation objects: multi-component and linear heterocyclization reactions of carbonyl compounds containing several reaction centers with polynucleophiles, chemical, physicochemical properties. Aim of the study: establishing regularities of multi-component reactions of carbonyl compounds with polynucleophiles, relationship between reaction parameters, starting compounds structure and heterocyclization direction, elaborating basics of their direction control strategy for selective formation of nitrogen containing heterocyclic systems. Methods of the study and apparatus: up-to-date organic synthesis utilizing thermal heating, microwave and ultrasound irradiation, photochemical reactions, a set of physico-chemical and spectral research methods. Theoretical and practical results: New regularities of heterocyclization reactions of polynucleophiles with carbonyl compounds have been established, basics of their direction control strategy have been elaborated, high-selective nitrogen containing heterocyclic systems synthesis methods have been proposed which develop the "ideal synthesis" concept and enable enlarging molecular diversity of organic compounds. Analyses of in vitro screening data for the presence of anti-tumor, antituberculous and antioxidant activities and in vivo for the presence of sugar-lowering action have been performed. Novelty: The possibility of heterocyclization reactions between aminoazoles and carbonyl methylene-active compounds for passing under both kinetic and thermodynamic control was established which enables to control their direction by varying temperature mode. The influence of acid-base properties of reaction mixture and catalyst type onto the composition of multicomponent reactions products was studied. New three- and four-component heterocyclization reactions enabling to synthesize previously unknown natural alkaloids analogs containing pyrazoloquinolyzine fragment or spiro-heterocyclic compounds in one-pot operation have been discovered. Degree of implementation: The data obtained in the dissertation were used for investigations of heterocyclic compounds chemistry department. Some methods of obtaining new compounds were used in synthesizing biologically active compounds in the Danilevsky Institute for Endocrine Pathology Problems. Range (branch) of application: Laboratories and departments of different educational and scientific institutions where researches of close thematic objects are carried out, scientific research centers for biological activity detection and studying.