Tetrahedron Letters p. 5133 - 5134 (1998)
Update date:2022-08-29
Topics:
Zhang
Tillekeratne
Hudson, Richard A.
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.
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