Radical cyclisation reactions with indoles
Radical cyclisation reactions with indoles
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.
menadione toxicity, cyclization, heterocycles, derivatives, alkaloids
1795-1798
Flanagan, S. R.
6a60460e-2572-4441-8693-6b591c5121aa
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bradley, M.
078a34d6-96c4-4ce1-9aa1-454d9ee0030d
24 February 2003
Flanagan, S. R.
6a60460e-2572-4441-8693-6b591c5121aa
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bradley, M.
078a34d6-96c4-4ce1-9aa1-454d9ee0030d
Flanagan, S. R., Harrowven, D. C. and Bradley, M.
(2003)
Radical cyclisation reactions with indoles.
Tetrahedron Letters, 44 (9), .
(doi:10.1016/S0040-4039(03)00094-7).
Abstract
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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Published date: 24 February 2003
Keywords:
menadione toxicity, cyclization, heterocycles, derivatives, alkaloids
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Local EPrints ID: 19952
URI: http://eprints.soton.ac.uk/id/eprint/19952
ISSN: 0040-4039
PURE UUID: 940fe7e0-2d43-4fc8-93f6-a98bfaf8312c
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Date deposited: 20 Feb 2006
Last modified: 16 Mar 2024 02:46
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Author:
S. R. Flanagan
Author:
M. Bradley
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