Nucleophilic Reactivity of a Novel 3-Chloro-3-(4,9-dimethoxy5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal

Abstract

A novel 3-chloro-3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal was synthesized from 6-acetyl-4,9-dimethoxy-5H-furo[3,2-g]chromen-5-one by the Vilsmeier–Haack reaction, and its chemical reactivity toward some mono- and di-nitrogen nucleophiles was investigated. The reactions of the synthesized enal with primary amines, specifically benzylamine and p-toluidine, gave novel enamines or enaminones, depending on the molar ratio of the reagents, and its reactions with 1,2- and 1,3-dinucleophiles produced some novel benzofuran derivatives bearing bipyrazole, pyrazolylisoxazole, and bipyrimidine substituents in the C position. The structures of the newly synthesized compounds waere elucidated on the basis of their analytical and spectral data.