A Straightforward Preparation of Benzindoles by an Intramolecular Diels-Alder Cycloaddition of Unsaturated Ketenimines.

DOI: 10.1016/S0040-4020(01)90414-4

Source and publish data:

Tetrahedron p. 5027 - 5036 (1994)

Update date:2022-09-26

Topics:

Authors:

Molina, Pedro

Lopez-Leonardo, Carmen

Alcantara, Julian

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Article abstract of DOI:10.1016/S0040-4020(01)90414-4

An intramolecular Diels-Alder cycloaddition of the ketenimines 3, available by aza Wittig reaction between iminophosphoranes 2, derived from azido olefins 1, and diaryl ketenes followed by an oxidative aromatization of the cycloadduct provided benzindoles 5.Attempts to apply this process either with ethylphenylketene, 5-aryl-4-pentenylazides or with the related carbodiimides failed.

Full text of DOI:10.1016/S0040-4020(01)90414-4

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