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Synthesis of 1,5-methano-2-benzazocines from 3-hydroxy-1,3-dimethyl-6-phenyl-4-piperidone

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reaction of 3e-hydroxy-1e,3a-dimethyl-6e-phenyl-4-piperidone with cyanoacetic ester affords 6e,8a-dimethyl-2-oxo-5e-phenyl-3-cyanofuro[2,3-c]piperidine, the epoxide of which undergoes intramolecular cyclization on treatment with 80% H2SO4, to give 1,2,5,6-tetrahydro-2-endo-4-dimethyl-1,5-methano-6-oxo-2-benzazocin-3-ene. It has been found that the latter is formed via the intermediate 3-hydroxy-6e,8a-dimethyl-2-oxo-5e-phenylfuro[2,3-c]piperidine.

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Authors and Affiliations

  1. V. I. Lenin Belorussian State University, 220080, Minsk

    G. V. Pshenichnyi, V. A. Mashenkov & L. S. Stanishevskii

Authors
  1. G. V. Pshenichnyi
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  2. V. A. Mashenkov
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  3. L. S. Stanishevskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1371–1374, October, 1986.

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Pshenichnyi, G.V., Mashenkov, V.A. & Stanishevskii, L.S. Synthesis of 1,5-methano-2-benzazocines from 3-hydroxy-1,3-dimethyl-6-phenyl-4-piperidone. Chem Heterocycl Compd 22, 1110–1113 (1986). https://doi.org/10.1007/BF00473490

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  • DOI: https://doi.org/10.1007/BF00473490

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