Russian Journal of General Chemistry

, Volume 74, Issue 8, pp 1277–1281 | Cite as

Adamantylazoles: VIII. Acid-catalyzed adamantylation of 1,2,4-triazol-5-ones

  • A. D. Amandurdyeva
  • V. V. Saraev
  • N. E. Kuz’mina
  • E. L. Golod


3-R-1,2,4-Triazol-5-ones are adamantylated in sulfuric acid. The reaction involves the N1 atom of the ring. 4-Adamantyl-1-methyl-, 1-adamantyl-4-methyl-, and 1,4-diadamantyl-1,2,4-triazol-5-ones were also prepared. Therewith, it was found that N1 exhibits a higher reactivity than N4.


Sulfuric Acid High Reactivity 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Gavrilov, A.S., Kachala, V.V., Kuz’mina, N.E., and Golod, E.L., Zh. Obshch. Khim., 2004, vol. 74, no.5, p. 819.Google Scholar
  2. 2.
    Chipen, G.I. and Bokalder, R.P., Khim. Geteretsikl. Soedin., 1969, no. 1, p. 159.Google Scholar
  3. 3.
    Kofman, T.P., Pevzner, M.S., Zhukova, L.N., Kravchenko, T.A., and Frolova, G.M., Zh. Org. Khim., 1980, vol. 16, no.2, p. 420.Google Scholar
  4. 4.
    Saraev, V.V., Kanakina, T.P., Pevzner, M.S., Golod, E.L., Ugrak, B.I., and Kachala, V.V., Khim. Geteretsikl. Soedin., 1996, no. 8, p. 1078.Google Scholar
  5. 5.
    Allen, F.N., Kennard, O., Watson, D.G., Brammer, L., and Orpen, A.G., J. Chem. Soc., Perkin Trans. 2, 1987, no. 12,suppl. S1, p. 1.Google Scholar
  6. 6.
    Madding, G.D., Smith, D.W., Sheldon, R.L., and Lee, B., J. Heterocycl. Chem., 1985, vol. 22, no.4, p. 1121.Google Scholar
  7. 7.
    Rae, A.D., Ramsay, C.G., and Steel, P.J., Aust. J. Chem., 1988, vol. 41, no.4, p. 419.Google Scholar
  8. 8.
    Kamiya, S., Yamaguchi, K., Miyahara, M., and Miyata, N., Chem. Pharm. Bull., 1990, vol. 38, no.12, p. 3226.Google Scholar
  9. 9.
    Amoureux, J.P. and Foulon, M., Acta Crystallogr., Sect. B, 1987, vol. 43, no.5, p. 470.Google Scholar
  10. 10.
    Pauling, L., The Nature of Chemical Bond and the Structure of Molecules and Crystals, London: Cornell Univ. Press, 1960.Google Scholar
  11. 11.
    Masunov, A.E. and Zorkii, P.M., Zh. Strukt. Khim., 1992, vol. 33, no.3, p. 105.Google Scholar
  12. 12.
    Sheldrick, G.M., SHELX 93. Program for refinement of crystal structures, Göttingen: Univ. of Göttingen, 1993.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • A. D. Amandurdyeva
    • 1
  • V. V. Saraev
    • 1
  • N. E. Kuz’mina
    • 1
  • E. L. Golod
    • 1
  1. 1.St. Petersburg State Institute of TechnologySt. PetersburgRussia

Personalised recommendations