The synthesis and some transformations of 2-(2-Furyl)-1H-naphto[2,3-d]imidazole

Abstract

2-(2-Furyl)-1H-naphto[2,3-d]imidazole was synthesised by interaction of 2,3-diaminonaphtalene with furfural in the conditions of Weidenhagen reaction. At its N-methylation in the KOH-DMSO system the 1-methyl-2-(2-furyl)-1H-naphto[2,3-d]imidazole was obtained, which we subjected to reactions of electrophilic substitution (nitration, bromination, sulfonation, formylation, and acylation). This compound possesses a specific reactivity: all reactions, as a rule, proceed at the naphthalene scaffold while the furan ring is not involved.