Solvent effects on the manganese (III) initiated oxidative free radical reactions of 2-amino-1, 4-naphthoquinones are described. This free radical reaction provides a novel method for the synthesis of benzo [f] indole-4, 9-diones, benzo [f] indole-2, 4, 9-triones, benzo [b] carbazole- 6, 11-diones and benzo [b] acridine-6, 11-diones. High chemoselectivity was observed in different solvents.