Synthesis of Hybrid Compounds on the Basis of 4-[(1-Oxo-3,4-dihydro-2H-naphthalen-2-ylidene)methyl]benzoic acid

Abstract

The reactions of 4-[(1-oxo-3,4-dihydro-2H-naphmalen-2-ylidene)methyl]benzoic acid with 3-(1,3-dioxobutane-1-yl)-2H-chromen-2-one in the presence of nitrogenous bases (piperidine, triethylamine or pyridine) were used to synthesize for the first time hybrid systems containing the pharmacophoric fragments of the reagents. The reaction scheme involves formation of a condensed dihydropyran structure and its subsequent aromatization into a benzodihydrochromenilium salt under the action of HCl. The process may be accompanied by the competing addition of an azanucleophile by the double bond of the chalcone.