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 electronrich 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 ...
