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Reaction of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol with 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

Upon heating in the presence of arylamines 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine decyclizes via a retroaldol type reaction with subsequent transamination of the intermediate Mannich base to give 3-arylamino-1-oxo-1-phenylpropanes. In the case of the use of arylhydrazines this γ-piperidol recyclizes to give 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectroscopic behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

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Authors and Affiliations

  1. Russian People’s Friendship University, Moscow, 117198

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

  2. M. V. Lomonosov State University, Moscow, 119899, 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 Anh
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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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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 544–554, April, 2007.

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Volkov, S.V., Kutyakov, S.V., Levov, A.N. et al. Reaction of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol with arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3 diarylpyrazoles and their fragmentation under electron impact. Chem Heterocycl Compd 43, 445–453 (2007). https://doi.org/10.1007/s10593-007-0064-3

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  • DOI: https://doi.org/10.1007/s10593-007-0064-3

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