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Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid

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Chemistry of Heterocyclic Compounds Aims and scope

1-[2-(Adamantan-1-yl)-2-hydroxyethyl]-1,2,3,6-tetrahydropyridines were obtained by reduction of 1-[(adamantan-1-yl)-2-oxoethyl]-pyridinium bromides. By the action of trifluoromethanesulfonic acid, they undergo carbocationic intramolecular cyclization accompanied by the Wagner–Meerwein rearrangement with the formation of substituted 1-azabicyclo[3.3.1]non-3-enes annulated with the homoadamantane framework. The structure of the obtained compounds was confirmed by spectral methods and X-ray structural analysis.

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St, Samara, 443100, Russia

    Vera А. Shadrikova, Evgeny V. Golovin & Yuri N. Klimochkin

  2. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Victor B. Rybakov

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  1. Vera А. Shadrikova
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  2. Evgeny V. Golovin
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  3. Victor B. Rybakov
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  4. Yuri N. Klimochkin
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Correspondence to Vera А. Shadrikova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 898–908

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Shadrikova, V.А., Golovin, E.V., Rybakov, V.B. et al. Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid. Chem Heterocycl Comp 56, 898–908 (2020). https://doi.org/10.1007/s10593-020-02747-9

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