The reactivity of indole-[3,4-b]-azepin-1,5-dione for halogenations and synthesis of alkylamine substituted indole-[3,4-b]-azepine derivatives

A novel method is developed for the synthesis of amine-substituted indole [3,4-b] azepine derivatives. In-situ chlorination, followed by nucleophilic substitution of 1,5-dichloro azepino[3,4-b] indole with respective amines yields the desired compounds. The reactivity of the azepinone ring toward chlorination reactions is intriguing and gives either rearranged or hydrolyzed products under aqueous work up conditions. In brominated azepinones, elimination is favored over nucleophilic substitution reaction. The synthesized compounds displayed in vitro cytotoxicity against human cancer cell lines.