Intramolecular radical cyclisations to pyridines


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).

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Description/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.

Item Type: Article
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Keywords: radicals and radical reactions, pyridines, nitrogen heterocycles, cascade reactionscondensed thiophenes, toddaquinoline, substitution, rings
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19508
Date Deposited: 14 Feb 2006
Last Modified: 27 Mar 2014 18:09
Contact Email Address: dch2@soton.ac.uk
URI: http://eprints.soton.ac.uk/id/eprint/19508

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