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Intramolecular radical cyclisations to pyridines

Intramolecular radical cyclisations to pyridines
Intramolecular radical cyclisations to pyridines
Intramolecular radical additions to the alpha-, beta- and gamma -carbons of a pyridine have each been shown to be facile processes. When a cis-alkene conjoins an ortho-iodoarene and a pyridine. radical cyclisation induced by homolysis of the carbon to iodine bond favours a 6-exo, endo-trig course. With a two carbon alkane conjoining the ortho-iodoarene and the pyridine, intermolecular hydrogen atom abstraction. 6-exo/endo-trig cyclisation and 5-exo-trig cyclisation modes compete. That the spirocyclic intermediates formed in the 5-exo-trig cyclisation rearrange with migration of the alkyl chain is noteworthy.
radicals and radical reactions, pyridines, nitrogen heterocycles, cascade reactionscondensed thiophenes, toddaquinoline, substitution, rings
0040-4039
9061-9064
Harrowven, D.C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Sutton, B.J.
8866e85f-472c-4644-b90e-08826b40c348
Coulton, S.
9d74c362-5867-4bef-ad9f-d3b819f042ca
Harrowven, D.C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Sutton, B.J.
8866e85f-472c-4644-b90e-08826b40c348
Coulton, S.
9d74c362-5867-4bef-ad9f-d3b819f042ca

Harrowven, D.C., Sutton, B.J. and Coulton, S. (2001) Intramolecular radical cyclisations to pyridines. Tetrahedron Letters, 42 (51), 9061-9064. (doi:10.1016/S0040-4039(01)01937-2).

Record type: Article

Abstract

Intramolecular radical additions to the alpha-, beta- and gamma -carbons of a pyridine have each been shown to be facile processes. When a cis-alkene conjoins an ortho-iodoarene and a pyridine. radical cyclisation induced by homolysis of the carbon to iodine bond favours a 6-exo, endo-trig course. With a two carbon alkane conjoining the ortho-iodoarene and the pyridine, intermolecular hydrogen atom abstraction. 6-exo/endo-trig cyclisation and 5-exo-trig cyclisation modes compete. That the spirocyclic intermediates formed in the 5-exo-trig cyclisation rearrange with migration of the alkyl chain is noteworthy.

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More information

Published date: 17 December 2001
Keywords: radicals and radical reactions, pyridines, nitrogen heterocycles, cascade reactionscondensed thiophenes, toddaquinoline, substitution, rings

Identifiers

Local EPrints ID: 19508
URI: http://eprints.soton.ac.uk/id/eprint/19508
ISSN: 0040-4039
PURE UUID: 1e285694-65f1-47a9-bf5b-e0826d3ba099
ORCID for D.C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 17 Dec 2019 01:59

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