Journal of the Chemical Society. Chemical communications p. 1224 - 1226 (1980)
Update date:2022-08-04
Topics: Synthesis Acylation Regioselectivity Heterocyclic compounds Deprotonation Organic synthesis Coumarin Carboxylic Acids Benzofuran Chromone VINYL CARBANIONS Flavone Anionic Intermediate Synthetic Methodology
Costa, Ana M. B. S. R. C. S.
Dean, Francis M.
Jones, Michael A.
Smith, Dennis A.
Varma, Rajender S.
Lithium di-isopropylamide at -70 deg C can remove the α-proton from benzofuran in the absence of activating groups and the β-proton if such groups are present; in flavone and 4-methoxycoumarin β-deprotonation occurs readily and the carbanions are easily carboxylated giving acids not previously accessible, while in 2,6-dimethylchromone β-deprotonation is kinetically favoured allowing 3-acylation to be achieved separately from the conventional acylation at the 2-methyl group.
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