AN UNUSUAL PRODUCT IN A DOEBNER-VONMILLER QUINOLINE SYNTHESIS

In an attempt to synthesize an aza pyrroloquinolinequinone isomer, Doe bner-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 beta to the ketone of dimethyl trans-2-oxoglutaconate. This observation suggests an alternative mech anistic possibility for Doebner-von Miller reaction with some electron -rich aromatic amines. (C) 1998 Elsevier Science Ltd. All rights reser ved.