Ring-closure of halogenonaphthoquinones by reaction with potassium 2-aminobenzenethiolate gave a series of naphthoquinoid infrared dyes which were useful as optical information recording media for semiconductor lasers. The ring-closure reaction was influenced mainly by the ring-substituents, by the quinone-quinoneimine tautomerism of the intermediates and also by the reaction conditions. Some of the tautomers were isolated and tautomerism in solution was also observed.