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Stereochemical aspects of pyrrole formation from substituted piperidin-4-one oximes and acetylene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Oxime derivatives of 1,2,5-trimethylpiperidin-4-one, 2-methyl-, and 2-(2-furyl)-4-ketodecahydroquinoline react with acetylene to form substituted pyrrolo[3,2-c]piperidines and their N-vinyl derivatives. During the course of pyrrolization the configuration at the 7-position is partially changed, resulting in the formation of two stereoisomeric pyrroles.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk

    B. A. Trofimov, A. M. Vasil'tsov, A. I. Mikhaleva, G. A. Kalabin, V. V. Shcherbakov, R. N. Nesterenko, E. A. Polubentsev & K. D. Praliev

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  1. B. A. Trofimov
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  2. A. M. Vasil'tsov
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  3. A. I. Mikhaleva
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  4. G. A. Kalabin
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  5. V. V. Shcherbakov
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  6. R. N. Nesterenko
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  7. E. A. Polubentsev
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  8. K. D. Praliev
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1365–1370, October, 1991.

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Trofimov, B.A., Vasil'tsov, A.M., Mikhaleva, A.I. et al. Stereochemical aspects of pyrrole formation from substituted piperidin-4-one oximes and acetylene. Chem Heterocycl Compd 27, 1095–1100 (1991). https://doi.org/10.1007/BF00486805

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  • DOI: https://doi.org/10.1007/BF00486805

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