Abstract
3- and 5-Furylcyclohexenones were obtained by the Michael reaction of furan chalcones with acetoacetic ester. Intermediate β-cycloketols were isolated in many cases. It was found that transformations of β-cycloketols by HClO4 and TrClO4 were a function of the nature of the substituent in position5 of the alicycle. 5-Arylketols undergo dehydration, while 5-furyl derivatives split both water and the furan fragment, resulting in aromatization of the alicycle. The structure of the synthesized compounds was confirmed by the IR and PMR spectra.
Similar content being viewed by others
References
K. B. Kawa, S. Ohasuki, and K. Kunematsu, Tetrahedron Lett.,27, No. 8, 947 (1986).
K. M. Mori and M. KatoTetrahedron Lett.27, No. 8, 981 (1986).
A. S. Kotnis, Tetrahedron Lett.,31, 481 (1990).
Y. Tamura and Y. Yoshimoto, Chem. Ind., 888 (1980).
E. B. Usova, G. D. Krapivin and V. G. Kul'nevich. Khim. Geterotsikl., Soedin, No. 9, 1289 (1992).
T. V. Stupnikova, L A. Rybenko, and Z. M. Skorobogatova, Khim. Geterotsikl. Soedin, No. 3,416 (1978).
E. B. Usova, L. I. Lysenko, G. D. Krapivin, and V. G. Kul'nevich Khim. Geterotsikl. Soedin., No. 11. 1577 (1993)
J. Brand and G. Eglinton, Use of Spectroscopy in Organic Chemistry [Russian translation]. Mir, Moscow (1967),p 162.
J. W. Emsley, J. Feeney, and L. H. Sutcliffe. High Resolution Nuclear Magnetic Resonance Spectroscopy, Vol. 2, Pergamon Press, Oxford (1966) [Russian translation V. F. Bystrov and Yu. N. Sheinker (eds.), Vol. 2, Mir, Moscow (l969), pp. 33-45]
Yu. Yu. Samitov, Khim. Geterotsikl. Soedin., No. 12, 1587(1978).
N. A. Orlova, T. N. Gerasimova, M. A. Kudinova, and A. I. Tolmachev, Zh. Org. Khim.,26, 1313 (1990).
Additional information
Kuban State Technological University, Krasnodar 350072. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 639–647, May, 1996. Original article submitted February 21, 1996.
Rights and permissions
About this article
Cite this article
Usova, E.B., Lysenko, L.I., Krapivin, G.D. et al. Furylcyclohexenones. 1. Synthesis and properties of 3- and 5-furyl-6-ethoxycarbonylcyclohexenones. Chem Heterocycl Compd 32, 548–554 (1996). https://doi.org/10.1007/BF01164783
Issue Date:
DOI: https://doi.org/10.1007/BF01164783