Intramolecular radical additions to pyridines
Intramolecular radical additions to pyridines
Intramolecular 6-exo/endo-trig and 5-exo-trig cyclisations of aryl radical intermediates to the alpha-, beta- and gamma-carbons of pyridine have been shown to be facile processes at neutral pH. The tether conjoining the radical donor to the pyridine plays an important role in determining the outcome of the reaction. When a Z-alkene is used as a tether, ortho-cyclisation proceeds in good yield. A more complex course is followed when a saturated two carbon tether is employed, leading to products derived from hydrogen atom abstraction, ipso-cyclisation and ortho-cyclisation pathways. All attempts to effect 5-exo/endo-trig cyclisations failed. Tributyltin hydride, tris(trimethylsilyl) silane, tris(trimethylsilyl) germane and, in part, samarium(II) iodide can each be employed as mediators of the reaction.
substitution-reactions, cyclization reactions, heteroaromatic bases, biaryls, series, route, toddaquinoline, derivatives, annulation, quinolines
4047-4057
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Sutton, Benjamin J.
ca6c5fe1-cdee-49b2-8e58-97d4d6072d50
Coulton, Steven
4935b9ef-822d-411d-8994-ed87d15ddc06
2003
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Sutton, Benjamin J.
ca6c5fe1-cdee-49b2-8e58-97d4d6072d50
Coulton, Steven
4935b9ef-822d-411d-8994-ed87d15ddc06
Harrowven, David C., Sutton, Benjamin J. and Coulton, Steven
(2003)
Intramolecular radical additions to pyridines.
Organic & Biomolecular Chemistry, 1 (22), .
(doi:10.1039/b309331j).
Abstract
Intramolecular 6-exo/endo-trig and 5-exo-trig cyclisations of aryl radical intermediates to the alpha-, beta- and gamma-carbons of pyridine have been shown to be facile processes at neutral pH. The tether conjoining the radical donor to the pyridine plays an important role in determining the outcome of the reaction. When a Z-alkene is used as a tether, ortho-cyclisation proceeds in good yield. A more complex course is followed when a saturated two carbon tether is employed, leading to products derived from hydrogen atom abstraction, ipso-cyclisation and ortho-cyclisation pathways. All attempts to effect 5-exo/endo-trig cyclisations failed. Tributyltin hydride, tris(trimethylsilyl) silane, tris(trimethylsilyl) germane and, in part, samarium(II) iodide can each be employed as mediators of the reaction.
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Published date: 2003
Keywords:
substitution-reactions, cyclization reactions, heteroaromatic bases, biaryls, series, route, toddaquinoline, derivatives, annulation, quinolines
Identifiers
Local EPrints ID: 19972
URI: http://eprints.soton.ac.uk/id/eprint/19972
ISSN: 1477-0520
PURE UUID: fc4007e4-0cfe-4001-a9d5-2eabccec9fa7
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Date deposited: 21 Feb 2006
Last modified: 16 Mar 2024 02:46
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Author:
Benjamin J. Sutton
Author:
Steven Coulton
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