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An unusual product in a Doebner-von Miller quinoline synthesis

✍ Scribed by Z.P. Zhang; L.M.V. Tillekeratne; Richard A. Hudson

Book ID: 104259501
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 109 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01008-9

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✦ Synopsis

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 [~ 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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