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Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It has been established that on heating, 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine is ring-opened in the presence of arylamines by a type of retroaldol reaction, with subsequent transamination of the intermediate Mannich base and the formation of 3-arylamino-1-oxo-1-phenylpropanes. When using arylhydrazines this γ-piperidol is recyclized with the formation of 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectral behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

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Authors and Affiliations

  1. Peoples’ Friendship University of Russia, Moscow, 117198

    S. V. Volkov, S. V. Kutyakov, A. N. Levov, E. I. Polyakova, Le Tuan An, S. A. Soldatova & A. T. Soldatenkov

  2. M. V. Lomonosov Moscow State University, Moscow, 119992, Russia

    P. B. Terentiev

Authors
  1. S. V. Volkov
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  2. S. V. Kutyakov
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  3. A. N. Levov
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  4. E. I. Polyakova
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  5. Le Tuan An
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  6. S. A. Soldatova
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  7. P. B. Terentiev
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  8. A. T. Soldatenkov
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Correspondence to S. V. Volkov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1486–1495, October, 2007.

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Volkov, S.V., Kutyakov, S.V., Levov, A.N. et al. Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact. Chem Heterocycl Comp 43, 1260–1268 (2007). https://doi.org/10.1007/s10593-007-0192-9

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  • DOI: https://doi.org/10.1007/s10593-007-0192-9

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