Cycvalone in the synthesis of nitrogen-, oxygen-containing heterocycles

Abstract

Cycvalone is an analogue of curcumin (EE conformation), exhibits a wide range of biological activity (antioxidant, hepatoprotective, membrane stabilizing, anti-ulcer) and is used in medical practice as a choleretic. Numerous methods of producing cycvalone are known, including industrial ones, but its reactions have been studied much less. Some reactions of cycvalone with N, C-nucleophiles (hydrazines, malononitrile) have been carried out. Reactions with getarylamines that could lead to the synthesis of compounds including pharmacophore fragments remained completely unexplored. We have used cycvalone as a substrate for the synthesis of nitrogen-, oxygen-containing heterosystems of a number of chromenopyrimidine, aminochromencarbonitrile, indazole, triazoloquinazoline. The structure of the obtained new substances has been established by spectral methods (IR, NMR). Schemes of formation of reaction products have been proposed.