Synthesis of novel pyrroloazepinones by Schmidt expansions of 6-indolones

Abstract

New derivatives of pyrroloazepinones were synthesized. The synthesis route consisted of three stages: the formation of a dimedone-derived tricarbonyl compound, the formation of a pyrrole ring resulting from the use of the Paal-Knorr method to generate tetrahydroindole-6-ones, and the expansion of the ketone by following the Schmidt method to generate lactams. The obtained 6-indolones were used to generate new derivatives: the pyrrolo[2,3-c]azepin-6-one and the pyrrolo[2,3-d]azepin-7-one ring systems. The synthesized pyrroloazepinones were evaluated for inhibitory activity in cancer cell lines and they did not show activity and cytotoxic effects on the non-tumor cells HEK239, with IC50 ≥ 215 ± 5.41 μM.