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Synthesis of 1-(Adamantan-1-yl)-1H-1,2,3-Triazoles and their Salts by Adamantylation in AdOH–HClO4 and AdOH–H2SO4 Systems

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Chemistry of Heterocyclic Compounds Aims and scope

1-(Adamantan-1-yl)-1H-1,2,3-triazoles and a series of 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salts were synthesized by regioselective adamantylation of 1,2,3-triazole derivatives. The direction of the attack by the adamantyl cation at the N-1 nitrogen atom and the regioselectivity of the processes of adamantylation and quaternization are ensured by a number of factors: the specificity of the properties of the high-acid systems AdOH–HClO4 and AdOH–H2SO4, as well as the structural aspect and high reactivity of adamantan-1-ol.

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Authors and Affiliations

  1. Institute for Problems of Chemical and Energy Technologies, Siberian Branch of the Russian Academy of Sciences, 1 Sotsialisticheskaya St., Biysk, 659322, Russia

    Gennady T. Sukhanov, Yuliya V. Filippova, Anna G. Sukhanova & Konstantin K. Bosov

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia

    Irina Yu. Bagryanskaya

  3. Novosibirsk State University, 2 Pirogova St., Novosibirsk, 630090, Russia

    Irina Yu. Bagryanskaya

Authors
  1. Gennady T. Sukhanov
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  2. Yuliya V. Filippova
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  3. Anna G. Sukhanova
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  4. Irina Yu. Bagryanskaya
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  5. Konstantin K. Bosov
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Correspondence to Yuliya V. Filippova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(12), 1197–1203

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Sukhanov, G.T., Filippova, Y.V., Sukhanova, A.G. et al. Synthesis of 1-(Adamantan-1-yl)-1H-1,2,3-Triazoles and their Salts by Adamantylation in AdOH–HClO4 and AdOH–H2SO4 Systems. Chem Heterocycl Comp 55, 1197–1203 (2019). https://doi.org/10.1007/s10593-019-02601-7

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