Russian Journal of Organic Chemistry

, Volume 49, Issue 8, pp 1135–1138 | Cite as

One-stage synthesis of adamantyl-containing α-aminonitriles

Article

Abstract

Reactions of 2-adamantan-2-one, acetone cyanohydrin, and amine lead to the formation of substituted 2-amino-2-cyanoadamantanes. The reaction is of a general character as has been proved by examples on a series of ketones and amines and it proceeds through the formation from the acetone cyanohydrin and amines of 2-amino-2-cyanopropane derivatives reacting further with the carbonyl compounds.

Keywords

Morpholine Potassium Carbonate Adamantyl Methyl Isobutyl Ketone Rimantadine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Morozov, I.S., Petrov, V.I., and Sergeeva, S.A., Farmakologiya adamantanov (Pharmacology of Adamantanes), Volgograd: Izd. Volgogr. Med. Akademii, 2001.Google Scholar
  2. 2.
    Zoidis, G., Kolocouris, N., Kelly, J.M., Prathalingam, S.R., Naesens, L., and Clercq, E.D., Eur. J. Med. Chem., 2010, vol. 45, p. 5022.CrossRefGoogle Scholar
  3. 3.
    Fytas, Ch., Zoidis, G., Tzoutzas, N., Taylor, M.C., Fytas, G., and Kelly, J.M., J. Med. Chem., 2011, vol. 54, p. 5250.CrossRefGoogle Scholar
  4. 4.
    Orere, D.M. and Reese, C.B., J. Chem. Soc., 1977, p. 280.Google Scholar
  5. 5.
    Evans, D.A., Truesdale, L.K., and Carroll, G.L., J. Chem. Soc., 1973, p. 55.Google Scholar
  6. 6.
    Popov, Yu.V., Mokhov, V.M., Tankabekyan, N.A., and Safronova, O.Yu., Zh. Prikl. Khim., 2012, vol. 85, p. 1474.Google Scholar
  7. 7.
    Popov, Yu.V., Mokhov, V.M., and Zimina, O.Yu., Izv. Volgogr. Gos. Tekhn. Iniv., 2008, vol. 5, p. 46.Google Scholar
  8. 8.
    Bucherer, H.Th. and Barsh, H., J. Prakt. Chem., 1934, p. 151.Google Scholar
  9. 9.
    Galletti, P., Pori, M., and Giacomini, D., Eur. J. Org. Chem., 2011, vols. 20–21, p. 3896.CrossRefGoogle Scholar
  10. 10.
    Yanovskaya, L.A., Shachidayatov, Ch., Prokofiev, E.P., Andrianova, G.M., and Kucherov, V.F., Tetrahedron, 1968, vol. 24, p. 4477.CrossRefGoogle Scholar
  11. 11.
    Shakhidayatov, Kh., Zh. Org. Khim., 1973, vol. 9, p. 1373.Google Scholar
  12. 12.
    Walter, V. and Hubner, U.. J. Prakt. Chem., 1916, vol. 93, p. 119.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • Yu. V. Popov
    • 1
  • V. M. Mokhov
    • 1
  • N. A. Tankabekyan
    • 1
  1. 1.Volgograd State Technical UniversityVolgogradRussia

Personalised recommendations