Free accessResearch articleFirst published online 2006-9
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.
HajelaK., and KapilR.S., Euro. J. Med. Chem., 1997, 32, 135.
2.
(a) HorinoH., MimuraT., KagechikaK., OhtaM., KuboH., and KitagawaM., Chem. Pharm. Bull., 1998, 46, 602; (b) R. Mannhold, G. Cruciani, H. Weber, H. Lemoine, A. Derix, C. Weichel and M. Clementi, J. Med. Chem., 1999, 42, 981; (c) M.J. Chen, Y.M. Lee, J.R. Sheu, C.T. Hu and M.H. Yen, J. Pharm. Pharmacol., 1998, 50, 83; (d) G.C. Rovnyak, S. Z. Ahmed, A.J. Baird, C.Z. Ding, S. Dzwonczyk, F.N. Ferrata and W.G. Humphreys, J. Med. Chem., 1997, 40, 24.
BoulletF.M., VilleminD., RicardM., MoisonA., and FoucaudA., Tetrahedron, 1985, 41, 1259.
13.
(a) WangX.S., ShiD.Q., and TuS.J., Synth. Commun., 2003, 33, 119; (b) X.S. Wang, D.Q. Shi, X.Y. Wei and Z.M. Zong, J. Chem. Res., 2004, 679; (c) X.S. Wang, D.Q. Shi, H.Z. Yu, G.F. Wang and S.J. Tu, Synth. Commun., 2004, 34, 509.
14.
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.
15.
SvetlikJ., PronayovaN., and HanusV., J. Heterocycl. Chem., 2000, 37, 395.
16.
OssamaD.S., KirstenA.G., QuangT., and RichardP.H.Tetrahedron Lett., 2001, 42, 3283.
