Synlett 2004(11): 1905-1908  
DOI: 10.1055/s-2004-830868
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indoles Using Cyclization of Imidoyl Radicals

W. Russell Bowman*a, Anthony J. Fletchera, Peter J. Lovellb, Jan M. Pedersena
a Department of Chemistry, Loughborough University, Loughborough, Leics. LE11 3TU, UK
Fax: +44(1509)223925; e-Mail: w.r.bowman@lboro.ac.uk;
b Psychiatry Medicinal Chemistry III, GlaxoSmithKline, New Frontiers Science Park North, Harlow, Essex CM19 5AW, UK
Further Information

Publication History

Received 20 May 2004
Publication Date:
04 August 2004 (online)

Abstract

Imidoyl radicals, generated from imidoyl phenylselanide precursors, have been used for the synthesis of 2,3-disubstituted indoles. A facile high yielding synthesis of imidoyl phenylselanides has been developed. The potential for neophyl rearrangement of 5-exo radical intermediates to 6-endo radical intermediates is discussed.

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We thank Professor Mario D. Bachi, Weizmann Institute, Rehevot, Israel for providing us with unpublished results.