Synthesis and some transformations of new 9-furylnaphtho[2,3- b]furan derivatives

Abstract

The synthesis of a number of naphtho[2,3- b]furan derivatives, containing a furyl substituent in position 9 by intramolecular cyclization of 2-carboxy and 2-formylbis(5-alkylfur-2-yl)methanes is described. The reactivity of the title compounds in formylation, acetylation, nitration, and oxidation reactions has been investigated. It was shown that nitration of 2-methyl-9-(5-methyl-2-furyl)naphtho[2,3- b]furan-4-yl acetate leads to oxidative furan ring opening rather than to electrophilic substitution.