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Adamantylation of 3-Nitro- and 3-Ethoxycarbonyl-1,2,4-triazolo[5,1-c]-1,2,4-triazin-4-ones

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Abstract

Reaction of 3-nitro- and 3-ethoxycarbonyl-1,2,4-triazolo[5,1-c]-1,2,4-triazin-4-ones with 1-adamantanol (or 1-adamantyl nitrate) in concentrated sulfuric acid or with 1-bromoadamantane in sulfolane affords N-adamantyl derivatives. The adamantylation of 3-nitro-1,4-dihydro-7H-1,2,4-triazolo[5,1-c]-1,2,4-triazin-4-one yields a mixture of N8- and N1-isomers that undergo interconversion in concentrated sulfuric acid along intermolecular mechanism.

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Authors and Affiliations

  1. Ural State Technical University, Yekaterinburg, 620002, Russia

    E. N. Ulomskii & S. L. Deev

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia

    A. V. Tkachev & V. L. Rusinov

  3. Samara State Technical University, Samara, Russia

    I. K. Moiseev

Authors
  1. E. N. Ulomskii
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  2. S. L. Deev
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  3. A. V. Tkachev
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  4. I. K. Moiseev
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  5. V. L. Rusinov
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Ulomskii, E.N., Deev, S.L., Tkachev, A.V. et al. Adamantylation of 3-Nitro- and 3-Ethoxycarbonyl-1,2,4-triazolo[5,1-c]-1,2,4-triazin-4-ones. Russian Journal of Organic Chemistry 38, 272–280 (2002). https://doi.org/10.1023/A:1015538322029

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  • DOI: https://doi.org/10.1023/A:1015538322029

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