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

Authors

  • С. В. Волков Peoples' Friendship University of Russia, Moscow 117198
  • С. В. Кутяков Peoples' Friendship University of Russia, Moscow 117198
  • А. Н. Левов Peoples' Friendship University of Russia, Moscow 117198
  • Е. И. Полякова Peoples' Friendship University of Russia, Moscow 117198
  • Ле Туан Ань Peoples' Friendship University of Russia, Moscow 117198
  • С. А. Солдатова Peoples' Friendship University of Russia, Moscow 117198
  • П. Б. Терентьев M. V. Lomonosov Moscow State University, Moscow 119992
  • А. Т. Солдатенков Peoples' Friendship University of Russia, Moscow 117198

DOI:

https://doi.org/10.1007/7366

Keywords:

arylamines, arylhydrazines, 3-arylamino-1-oxo-1-phenylpropanes, 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine, 1, 3-diarylpyrazoles, mass spectra

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.

How to Cite
Volkov, S. V.; Kutyakov, S. V.; Levov, A. N.; Polyakova, E. I.; An, L. T.;  Soldatova, S. A.; Terentiev, P. B.; Soldatenkov, A. T.  Chem. Heterocycl. Compd. 2007, 43, 1260. [Khim. Geterotsikl. Soedin. 2007, 1486.]

For this article in the English edition see DOI 10.1007/s10593-007-0192-9


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Published

2023-01-25

Issue

No. 10 (2007)

Section

Original Papers