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Communication | Regular issue | Vol 43, No. 4, 1996, pp.745-749
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7341
An Efficient Synthesis of Reduced Flavones via Diels-Alder Addition to 4H-Pyran-4-ones

Paul W. Groundwater, David E. Hibbs, Michael B. Hursthouse, and Miklós Nyerges*

*Department of Chemistry, Unvierity of Wales Cardiff, P. O. Box 912, Cardiff CF1 3TB, U. K.


The 4H-pyran-4-one (4c) undergoes Diels-Alder cycloaddition with electron-rich dienes to give the reduced flavones (7), whereas the pyran-4-one (4b) and 2-phenyl-4H-pyran-4-one (4a) are unreactive. The 3D structure of the adduct 7a of 4c with Danishefsky’s diene (6a) was confirmed by X-ray crystallography.