Abstract
An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.
Original language | English |
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Pages (from-to) | 954-971 |
Number of pages | 18 |
Journal | Journal of Heterocyclic Chemistry |
Volume | 51 |
Issue number | 4 |
DOIs | |
State | Published - Jul 2014 |