Sakhno Y. Heterocyclization reactions of pyruvic acid and its derivatives with aminoazoles

Investigation objects: pyruvic acid, aryl- and arylidenepyruvic asids, aminoazoles, aromatic aldehydes, azolo[1,5-a]pyrimidine-5-, azolo[4,3-a]pyrimidine-7-, pyrazolo[3,4-b]pyridine-6-, pyrazolo[3,4-b]pyridine-4-carboxylic acids. Objectives: study of heterocyclization reactions of pyruvic acids with aminoazoles, disclosure of their regularities, development of novel selective preparative synthetic methods for fused pyridine and pyrimidine derivatives containing carboxylic group. Methods: organic synthesis, NMR spectroscopy, mass-spectrometry, high-performance liquid chromatography, X-ray crystallography, elemental analysis. The detailed study of reactions involving pyruvic acids and aminoazoles was carried out and general regularities of their passing enabling to develop principles of tuning their regioselectivity were determined. Essential influence of temperature on reactions regioselectivity was shown and possibility of their thermodynamic and kinetic control was disclosed. It was found for the first time that reactions of arylidenepyruvic acids or their synthetic precursors pass according to alternative mechanisms and in the most cases lead to formation of heterocycles with different regioselectivity. A series of new pyridine- and pyrimidine carboxylic acids derivatives was synthesized as well as pyrrolone and furanone derivatives. Some types of biological activity of the compounds synthesized were estimated. Implementation degree: Some methods of obtaining new substances were used in synthesis of biologically active compounds in the Danilevsky Institute of Endocrine Pathology Problems AMS of Ukraine (act of application 2008.09.10).