Abstract
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 amines.
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