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Synthesis of azetidin-3-ones by heterocyclization of α-cyclohexylamino-α′,Β′-epoxy ketones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The stereospecific cyclization of 5-aryl-2-methyl-5-methoxy-4-cyclohexylamino-1,2-epoxypentan-3-one borofluorides on heating in acetone or in acetonitrile leads to 4-arylmethoxymethyl-2-hydroxymethyl-2-methyl-1-cyclohexyl-azetidin-3-ones. Certain chemical transformations of the latter have been studied. It was shown that, in contrast to the borofluoride complex, 2-methyl-5-methoxy-5-phenyl-4-cyclohexylamino-1,2-epoxypentan-3-one cyclizes into a mixture of diastereomeric 2-(cyclohexylamino)tetrahydrofuran-3-ones.

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Authors and Affiliations

  1. Scientific Research Institute of Physicochemical Problems at V. I. Lenin Belorussian State University, 220,080, Minsk

    A. M. Zvonok, N. M. Kuz'menok & L. S. Stanishevskii

Authors
  1. A. M. Zvonok
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  2. N. M. Kuz'menok
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  3. L. S. Stanishevskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 24, No. 3, pp. 307–312, March, 1988.

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Zvonok, A.M., Kuz'menok, N.M. & Stanishevskii, L.S. Synthesis of azetidin-3-ones by heterocyclization of α-cyclohexylamino-α′,Β′-epoxy ketones. Chem Heterocycl Compd 24, 250–255 (1988). https://doi.org/10.1007/BF00475317

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  • DOI: https://doi.org/10.1007/BF00475317

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