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Furylcyclohexenones. 1. Synthesis and properties of 3- and 5-furyl-6-ethoxycarbonylcyclohexenones

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors
  1. E. B. Usova
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  2. L. I. Lysenko
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  3. G. D. Krapivin
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  4. V. G. Kul'nevich
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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.

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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

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  • DOI: https://doi.org/10.1007/BF01164783

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