Tandem reactions via Barton esters with intermolecular addition and vinyl radical substitution onto indole

Coyle, Robert, McArdle, Patrick and Aldabbagh, Fawaz (2014) Tandem reactions via Barton esters with intermolecular addition and vinyl radical substitution onto indole. The Journal of Organic Chemistry, 79(12), pp. 5903-5907. ISSN (print) 0022-3263

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Abstract

A one-pot initiator-free Barton ester decomposition with tandem radical addition onto alkyl propiolates or phenylacetylene with aromatic substitution of the resultant vinyl radical allows convenient access to new 9-substituted 6,7-dihydropyrido[1,2-a]indoles. Propyl radical cyclizations compete when forming the expanded 7,8-dihydro-6H-azepino[1,2-a]indole system. 2-Thiopyridinyl S-radical is incorporated into aromatic adducts when using unsubstituted indole-1-alkanoic acid precursors. X-ray crystallography on substitution products allows selectivity of the radical addition onto less reactive internal alkynes to be determined.

Item Type: Article
Research Area: Chemistry
Faculty, School or Research Centre: Faculty of Science, Engineering and Computing (until 2017) > School of Pharmacy and Chemistry
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Depositing User: Fawaz Al-Dabbagh
Date Deposited: 02 Nov 2017 16:25
Last Modified: 02 Nov 2017 16:25
DOI: https://doi.org/10.1021/jo5008543
URI: http://eprints.kingston.ac.uk/id/eprint/39344

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