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

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.

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