Pitkovych K. Arylation five- and sixmembered heterocyclics by arenediazonium salts and transformation of the products of the reactions

This scientific work is devoted to development of new methods for the synthesis of aryl substituted heterocycles and for subsequent transformations of obtained compounds. The main attention is paid to the study of heterocyclic compounds under Meerwein arylation conditions, since it is a convenient and cheap option of cross-coupling reactions. For the first time interaction of 1-methylpyridine-2-one, 5-bromopyridine-2-one, 1-methylquinolin-2-one, pyran-2-one, pyran-4-one, 3- and 7-hydroxycoumarines with arenediazonium salts under the copper-catalyzed conditions was investigated. It was found that arylation of the mentioned heterocycles proceeds under these conditions selectively in one position. The behavior of pyrano[2,3-c]pyrazolone in the metal-catalyzed reaction with arenediazonium salts was investigated. It was shown that the Meerwein reaction can be applied to some mesoionic compounds (3-arylsydnones, benzofuroxane) which undergo arylation in the 4 position. It was found that copper- catalyzed arylation of ethyl 4-(pyrrol-1-yl)benzoate with arenediazonium salts leads to formation of 4-[(5Z)-2-oxo-5-(arylhydrazono)-2,5-dihydro-1H-pyrrol-1-yl]benzoates. It was found that obtained arylsubstituted heterocycles are suitable reagents for further transformations. It was shown that obtained 3-(4-bromophenyl)-1-methylquinolin-2(1H)-one is a convenient reagent for Suzuki coupling reaction with a boronic acids. 3-(4-Bromophenyl)-7-methoxy-2H-chromen-2-one and 3-(4-bromophenyl)-2H-chromen-2-one were investigated in Ullmann reaction with carbazole. Obtained in such way carbazole-coumarin dyes show prominent photophysical properties. For series of synthesized compounds antimicrobial and antifungal activities were tested. Separate representatives show significant antimicrobial and antifungal properties.