Radical cyclisation reactions with indoles

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).


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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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(03)00094-7
ISSNs: 0040-4039 (print)
Keywords: menadione toxicity, cyclization, heterocycles, derivatives, alkaloids
ePrint ID: 19952
Date :
Date Event
24 February 2003Published
Date Deposited: 20 Feb 2006
Last Modified: 16 Apr 2017 23:00
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/19952

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