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■ The Preparation and Rearrangement of 1-Prenylindoles and 3-Prenylindolenines

Kenneth J. Baird, Michael F. Grundon, David M. Harrison, and M. Gerard Magee

*School of Physical Sciences, New University of Ulster, Coleraine Northern Ireland, U.K.

Abstract

The preparation of 3-alkyl-3-prenylindolenines was explored by rearrangement of 1-prenylindoles and by allylation of 2-(methylthio)indoles. Reaction of the 3-formylindole (6) with trifluoracetic acid gave first the addition product (7) and then the pyridinoindole (8); the esters (11) and (14) were formed similarly from the tryptophan derivative (10) and the 2-(methylthio)indolenine (13), respectively. Successive reaction of the indolenine (13) with lithium aluminium hydride and manganese dioxide gave 3-(3,3-dimethylallyl)-3-methylindolenine (18) in good yield.