A STRAIGHTFORWARD PREPARATION OF BENZ[F]INDOLES BY AN INTRAMOLECULAR DIELS-ALDER CYCLOADDITION OF UNSATURATED KETENIMINES

Authors
MOLINA P LOPEZLEONARDO C ALCANTARA J
Citation
P. Molina et al., A STRAIGHTFORWARD PREPARATION OF BENZ[F]INDOLES BY AN INTRAMOLECULAR DIELS-ALDER CYCLOADDITION OF UNSATURATED KETENIMINES, Tetrahedron, 50(17), 1994, pp. 5027-5036
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
17
Year of publication
1994
Pages
5027 - 5036
Database
ISI
SICI code
0040-4020(1994)50:17<5027:ASPOBB>2.0.ZU;2-P
Abstract
An intramolecular Diels-Alder cycloaddition of de ketenimines 3, avail able by aza Wittig reaction between iminophosphoranes 2, derived from azido olefins 1, and diaryl ketenes followed by an oxidative aromatiza tion of the cycloadduct provided benz[f]indoles 5. Attempts to apply t his process either with ethylphenylketen, 5-aryl-4-pentenylazides or w ith the related carbodiimides failed.