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Oxidative Reactions of Azines. 11. The Influence of Manganese Dioxide on the Reaction of Tetrahydropyridines with Formaldehyde: Synthesis and Molecular Structures of 3-Oxa-7-azabicyclo[3.3.1]- and 6-Oxa-2-azabicyclo[3.2.1]octanes

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Abstract

New derivatives of piperidino[4,5-d]dioxane and 3-oxa-7-bicyclo[3.3.1]nonane were obtained by the oxidatively catalysed condensation of 4-aryl-1,2,3,6-tetrahydropyridines with formaldehyde. The direction of this reaction is sharply altered in the presence of manganese dioxide to give 6-oxa-2-azabicylo[3.2.1]octan-4-one — the product of the oxidative condensation of a new type.

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Authors and Affiliations

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

    A. T. Soldatenkov, K. B. Polyanskii, A. V. Temesgen, N. D. Sergeeva, V. V. Vysotskaya & B. B. Averkiev

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

    M. Yu. Antipin & N. N. Lobanov

Authors
  1. A. T. Soldatenkov
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  2. K. B. Polyanskii
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  3. A. V. Temesgen
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  4. N. D. Sergeeva
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  5. V. V. Vysotskaya
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  6. B. B. Averkiev
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  7. M. Yu. Antipin
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  8. N. N. Lobanov
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Soldatenkov, A.T., Polyanskii, K.B., Temesgen, A.V. et al. Oxidative Reactions of Azines. 11. The Influence of Manganese Dioxide on the Reaction of Tetrahydropyridines with Formaldehyde: Synthesis and Molecular Structures of 3-Oxa-7-azabicyclo[3.3.1]- and 6-Oxa-2-azabicyclo[3.2.1]octanes. Chemistry of Heterocyclic Compounds 40, 641–649 (2004). https://doi.org/10.1023/B:COHC.0000037321.18924.c0

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  • DOI: https://doi.org/10.1023/B:COHC.0000037321.18924.c0

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