A useful method for a molecular iodine induced 1,3-dipolar cycloaddition/oxidative aromatization sequence to construct 2-substituted-benzo[f]isoindole-1,3-dicarboxylates is reported. This is the first report of a molecular iodine induced 1,3-dipolar cycloaddition between quinone structures and diethyl N-substituted iminodiacetates.