N-Iodosuccinimide — An effective reagent for regioselective heterocyclization of o-cyclohex-2′-enylanilines for the synthesis of hexahydrocarbazoles

Abstract

A number of carbazoles are synthesized in good yields by the N-iodosuccinimide mediated heterocyclization of o-cyclohex-2′-enylanilines in acetonitrile at –10 °C for 45 min followed by heating with palladium–charcoal (10%) in benzene (80 °C) for 18–20 h.Key words: N-iodosuccinimide, hexahydrocarbazole, heterocyclization, carbazole, Claisen rearrangement.