Hydrolytic products of 4-aryl-2,3-dicyano-1-naphthol derivatives

Abstract

Depending on the conditions of hydrolysis, vicinal aromatic dicyano derivatives Ia-Ic gave anhydrides IIa-IIe and imides of 4-aryl-1-alkoxynaphthalene-2,3-dicarboxylic acids, IIIa,b, along with products of partial hydrolysis, decarboxylation and demethylation, IVa-IVd, IVf-IVg, and derivatives of benzo(c)fluorene, Va-Vc. The derivatives Va-Vc were also obtained by acid hydrolysis of dicyano derivatives Id-Ig. Methanolysis of the anhydride IId gave a mixture of positional isomers, IVh, which was esterified to the diester IVe. Intramolecular ring closure of the isomers IVh afforded derivatives of benzo(c)fluorene, VIa-VIb. The structures of the selected compounds were corroborated by IR and 1H NMR spectra. The compounds Va-Vc exhibited antiviral effects and interferonogenic activities in vivo.