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Oxidizing Reactions of Azines. 7. Imination of 4-Aryl-1,2,3,6-tetrahydropyridines by Arylamines in the Presence of Potassium Permanganate. Molecular Structure of 1-Methyl-2-(4-nitrophenylimino)-4-phenyl-1,2,5,6-tetrahydropyridine

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Abstract

On treating 4-aryl substituted 1-methyl-1,2,3,6-tetrahydropyridines with potassium permanganate in the presence of arylamines a previously unknown intermolecular oxidative imination reaction occurs leading to the formation of 2-(arylimino)-1,2,5,6-tetrahydropyridines. The molecular structure of 1-methyl-2-(4-nitrophenylimino)-4-phenyl-1,2,5,6-tetrahydropyridine was studied by X-ray analysis and it was shown that the hydropyridine ring of the molecule has a sofa conformation and its amidine fragment is in the E-configuration.

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Authors and Affiliations

  1. Russian Peoples' Friendship University, Moscow, 117198

    A. T. Soldatenkov, T. P. Khristoforova, A. W. Temesgen, B. N. Anissimov & M. Yu. Antipin

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, 117813

    B. B Averkiev, L. N. Kuleshova & V. N. Khrustalev

Authors
  1. A. T. Soldatenkov
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  2. T. P. Khristoforova
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  3. A. W. Temesgen
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  4. B. N. Anissimov
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  5. B. B Averkiev
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  6. L. N. Kuleshova
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  7. V. N. Khrustalev
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  8. M. Yu. Antipin
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Soldatenkov, A.T., Khristoforova, T.P., Temesgen, A.W. et al. Oxidizing Reactions of Azines. 7. Imination of 4-Aryl-1,2,3,6-tetrahydropyridines by Arylamines in the Presence of Potassium Permanganate. Molecular Structure of 1-Methyl-2-(4-nitrophenylimino)-4-phenyl-1,2,5,6-tetrahydropyridine. Chemistry of Heterocyclic Compounds 37, 715–722 (2001). https://doi.org/10.1023/A:1011965312855

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