Issue 23, 2003
From the journal:

Organic & Biomolecular Chemistry

Intramolecular addition of benzylic radicals onto ketenimines. Synthesis of 2-alkylindoles

Mateo Alajarín,a   Angel Vidal*a  and  María-Mar Ortína  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, 30100 Murcia, Spain
E-mail: vidal@um.es
Fax: 34 968 364149
Tel: 34 968 367418

Abstract

The inter- and intramolecular addition of free radicals onto ketenimines is studied. All the attempts to add intermolecularly several silicon, oxygen or carbon centered radicals to N-(4-methylphenyl)-C,C-diphenyl ketenimine were unsuccessful. In contrast, the intramolecular addition of benzylic radicals, generated from xanthates, onto the central carbon of a ketenimine function with its N atom linked to the ortho position of the aromatic ring occurred under a variety of reaction conditions. These intramolecular cyclizations provide a novel radical-mediated synthesis of 2-alkylindoles.

Graphical abstract: Intramolecular addition of benzylic radicals onto ketenimines. Synthesis of 2-alkylindoles

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Article information

DOI
https://doi.org/10.1039/B310593H
Article type
Paper
Submitted
03 Sep 2003
Accepted
01 Oct 2003
First published
23 Oct 2003

Org. Biomol. Chem., 2003,1, 4282-4292

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Intramolecular addition of benzylic radicals onto ketenimines. Synthesis of 2-alkylindoles

M. Alajarín, A. Vidal and M. Ortín, Org. Biomol. Chem., 2003, 1, 4282 DOI: 10.1039/B310593H

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