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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| Authors: | S V Volkov S V Kutyakov A N Levov E I Polyakova Le Tuan An S A Soldatova P B Terentiev A T Soldatenkov |
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| Institution: | (1) Peoples’ Friendship University of Russia, Moscow, 117198;(2) M. V. Lomonosov Moscow State University, Moscow, 119992, Russia |
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| 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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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1486–1495, October, 2007. |
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| Keywords: | arylamines arylhydrazines 3-arylamino-1-oxo-1-phenylpropanes 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine 1 3-diarylpyrazoles mass spectra |
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