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Issue 9, 1989
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Flavonoid epoxides. Part 18. Solvolysis products of 2-arylmethylenebenzo[b]furan-3(2H)-one (aurone) epoxides

Abstract

Aurone epoxides readily undergo solvolysis with aqueous acetone, methanol, and ethanol under neutral conditions, and also with acetic acid to give α,β-dihydroxy, α-hydroxy-β-alkoxy, and α-hydroxy-β-acetoxy aurones, which equilibrate in solution, through ring-chain tautomerism (Scheme 1), giving predominantly the cyclic benzofuranone diastereoisomers of the solvolysis products. Acetyl derivatives of the cyclic products and quinoxaline derivatives of the open-chain products have been prepared and characterised. Methanolysis of aurone epoxides under acid conditions gave α-methoxy-β-hydroxyaurone derivatives. 1H N.m.r. spectroscopy was used in the tentative assignment of the configurations of the solvolysis products.

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Article type: Paper
DOI: 10.1039/P19890001557
J. Chem. Soc., Perkin Trans. 1, 1989, 1557-1562

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    Flavonoid epoxides. Part 18. Solvolysis products of 2-arylmethylenebenzo[b]furan-3(2H)-one (aurone) epoxides

    B. A. Brady, M. Geoghegan and W. I. O'Sullivan, J. Chem. Soc., Perkin Trans. 1, 1989, 1557
    DOI: 10.1039/P19890001557

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