An unusual product in a Doebner-von Miller quinoline synthesis

Article abstract of DOI:10.1016/S0040-4039(98)01008-9

In an attempt to synthesize an aza pyrroloquinolinequinone isomer, Doebner-von Miller quinoline synthesis from an aminoindole resulted in an unexpected product, formed by reaction at an electron-rich benzenoid carbon with the unsaturated carbon atom β to the ketone of dimethyl trans-2- oxoglutaconate. This observation suggests an alternative mechanistic possibility for Doebner-von Miller reaction with some electron-rich aromatic amines.