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.

Keywords

• cycvalone
• chromenpyrimidinones
• 2-amino-4h-chromencarbonitriles
• azoloquinazolines
• condensation
• acylation
• spectra