Dyachenko I. Synthesis and properties of carbo[c]annelated poly-functional pyridines.

The thesis is devoted to the synthesis of functionalized carbo[c]annelated pyridines based enaminoketones and CH-acids, establishing the structure of the obtained compounds and study their properties. Based on the reaction of nucleophilic vinyl substitution (SNVin) convenient method of synthesis of previously unknown 3-carbamoyl-2-thioxo-, 3-N-aryl(alkyl)carbomoyl-2-thioxo-, N-aryl(alkyl)-3-cyano-2-oxo-, 3-thiocarbamoyl-2-thioxo-, 3-cyano-2-oxo-, 3-cyano-2-dicyanomethyliden- and 3-ethoxycarbonyl-2-thioxofunctionalized carbo[c]annelated pyridines. The observed regioselectivity process of C-, N-, O-, S-alkylation of functionalized carbo[c]annelated condensed pyridines and their derivatives, resulting in the formation of previously unknown esters, thioesters, N1-alkilpirazolopyridines and 1-amino-2-(4-bromobenzoyl)-5-(2-chlorophenyl)-6,7,8,9-tetrahydro-3Н-cyclopenta[c]isoquinoline-3,3-dicarbonitrile. Done screening carboxylic derivatives carbo[c]annelated pyridines which revealed among these compounds with pronounced bioactivity: 1-amino-5-isopropyl-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carbonitrile inhibits cell growth of skin cancer, 1-methyl-3-thioxo-2,3,5,6,7,8-hexaisoquinoline-4-carboxamide and 1-phenyl-3-thioxo-2,3,5,6,7,8-hexaisoquinoline-4-carboxamide marked fungicidal and antibacterial properties.