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Radical cyclisation reactions with indoles

Record type: Article

Several radical cyclisation reactions involving indoles are described. Most notably, we have shown that radical additions to C3 of an indole are frequently facile. A dichotomy in the course of radical cyclisation reactions to C2 of the indole has also been exposed wherein 6-endo-trig cyclisations are propagated by the loss of a hydrogen atom from C2 while 5-exo-trig cyclisations are propagated by hydrogen atom abstraction at C3 from tributyltin hydride. Cyclisations involving the addition of indolyl radical intermediates to arenes have also been demonstrated.

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Citation

Flanagan, S. R., Harrowven, D. C. and Bradley, M. (2003) Radical cyclisation reactions with indoles Tetrahedron Letters, 44, (9), pp. 1795-1798. (doi:10.1016/S0040-4039(03)00094-7).

More information

Published date: 24 February 2003
Keywords: menadione toxicity, cyclization, heterocycles, derivatives, alkaloids

Identifiers

Local EPrints ID: 19952
URI: http://eprints.soton.ac.uk/id/eprint/19952
ISSN: 0040-4039
PURE UUID: 940fe7e0-2d43-4fc8-93f6-a98bfaf8312c

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 17 Jul 2017 16:30

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Contributors

Author: S. R. Flanagan
Author: D. C. Harrowven
Author: M. Bradley

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