Decomposition of some substituted azidoindoles and azidohexahydrocarbazoles

Abstract

Photolytic and thermal decomposition of some substituted azidoindoles and azidohexahydrocarbazoles in nucleophilic solvents yields synthetically useful o-substituted aminoindoles. The conversion of 9-acetyl-7-azidohexahydrodarbazole in secondary amines on irradiation into an indoloazepine provides the first example of the expansion of a tricyclic hetero-system via a nitrene intermediate. Some cycloaddition reactions of these azides with dimethyl acetylenedicarboxylate are also reported.