Fischer indolization of N(α)-alkyl-2-allylphenylhydrazones

DOI: 10.1248/cpb.41.816

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 816 - 821 (1993)

Update date:2022-08-04

Topics:

Authors:

Katayama

Takatsu Takatsu

Takeuchi

Yamagiwa

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Article abstract of DOI:10.1248/cpb.41.816

Fischer indolization of the hydrazones of 8-allyl-1-amino-1,2,3,4-tetrahydroquinoline and related compounds was investigated. Fischer indolization induced Cope rearrangement of the allyl group and acid-catalyzed intramolecular cycloaddition between the hydrazonyl group and the vinyl group. The base treatment of the latter reaction product caused eliminative ring-opening of the adduct and led to the formation of an indoline skeleton bearing a 2-ketoalkyl group at the C-2 position.

Full text of DOI:10.1248/cpb.41.816

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