Moskvina V. Heterocyclic systems (O-, N-, S-containing) based on 4-arylcoumarins: synthesis and properties

The thesis is dedicated to the synthesis of new derivatives of pyranoneoflavones, furopyranoneoflavones, pyranochromenediones with thiazole residues, spirothiadiazolylpyranoneoflavones, heterocyclic derivatives of neoflavone (4-arylcoumarin) with pyrazole, N methylpyrazole, isoxazole, and pyrimidine residues, and also to the research of possibilities for further modification of obtained compounds, and their physicochemical properties. Modification at the C-2 exocyclic oxygen atom of the coumarin cycle was accomplished through spyropyranoneoflavones thioderivatives. Modification at the C-6 exocyclic oxygen atom of the pyran cycle was accomplished by treatment of a corresponding pyranoneoflavone with hydrazine, hydroxylamine, and thiosemicarbazides. Pyranochromenediones of both linear and angular structure were obtained by condensation of o-hydroxyformyl(acetyl)neoflavones with active methylene containing compounds, and also by intramolecular cyclization of neoflavone enamino ketones. For the first time heterocyclization of neoflavone enamino ketones with hydrazine, hydroxylamine, and amidines was used for the synthesis of 6- and 8 pyrazolyl-, isoxazolyl-, pyrimidinylneoflavones. 6- And 8-aminopyrazolyl-carbonylneoflavones as well as 6- and 8-aminocarbonitrylpyrimidinylneoflavones were obtained by recyclization of isoxazol-5-ylneoflavones when sequentially treated with DMFDMA and 1,2-N,N-, 1,3-N,N-binucleophiles.