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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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