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.
Original language | English |
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Pages (from-to) | 5903-5907 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 79 |
Issue number | 12 |
DOIs | |
Publication status | Published - 20 Jun 2014 |
Externally published | Yes |