Unexpected Ring-Opening of a 2-Pyrone Ring in the Synthesis of 3-[( Z )-1-Hydroxy-3-Oxobut-1-Enyl]-2 H -chromen-2-One Derivatives Catalysed by Kf-Alumina
Free accessResearch articleFirst published online September, 2006
Unexpected Ring-Opening of a 2-Pyrone Ring in the Synthesis of 3-[( Z )-1-Hydroxy-3-Oxobut-1-Enyl]-2 H -chromen-2-One Derivatives Catalysed by Kf-Alumina
A series of 3-[(Z)-1-hydroxy-3-oxobutenyl]-2H-chromen-2-one derivatives were synthesised by an unexpected ring-opening of a 2-pyrone ring reaction of substituted salicylaldehydes, and 4-hydroxy-6-methyl-pyran-2-one in ethyl alcohol at room temperature catalysed by KF-Al2O3. The enol structure of the product not ketone was characterised by 1H NMR, IR and elemental analysis, and enol and (Z)-structure further confirmed by X-ray diffraction analysis.
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X-ray crystallography for 3a: Crystallographic data for the structure 3a reported in this paper has been deposited at the Cambridge Crystallographic Data Centre as supplementary publication with No. CCDC-282532. Copies of available material can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0) 1223-336033 or e-mail: deposit@ccdc.cam.ac.uk). Empirical formula C13H10O4, FW = 230.21, T = 193(2) K, triclinic, space group P-1, a = 6.7577 (19) Å, b = 8.799 (3) Å, c = 9.890 (4) Å, α = 83.17(4), β = 76.17(3), γ = 71.10(3) °, V = 539.7(3) Å3, Z = 2, Dc = 1.417 Mg/m3, λ(MoKα) = 0.71070Å, μ = 0.106 mm−1, F(000) = 240, 3.17°<θ<25.35°, R = 0.0583, wR = 0.1526. S = 1.078, Largest diff. Peak and hole: 0.39 and −0.23 e·Å−3. The non-hydrogen atoms were refined anisotropically, the hydrogen atoms were positioned geometrically and refined as riding.
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