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Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 650–657 | Cite as

One-Pot Synthesis of N-Substituted Alkylaminocyclohexanols by the Addition of Electrophiles Formed in situ in the System Н2О2 + HBr (HCl)

  • O. A. Sadygov
  • Kh. M. Alimardanov
  • Sh. I. Ismailova
  • N. R. Babaev
Article
  • 5 Downloads

Abstract

Highly selective one-pot synthesis of N-substituted aminocyclohexanols has been performed by hydroxyhalogenation of the corresponding cyclohexenes with electrophilic reagents formed in situ in the system Н2О2 + HHlg (Hlg = Cl, Br), with subsequent substitution of halogen atoms with amines. Some products were tested as antimicrobial additives to motor oils and cooling lubricants and showed high antibacterial and antifungal activity.

Keywords

hydroxyhalogenation electrophilic intermediates aminocyclohexanols alicyclic aminoalcohols 

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References

  1. 1.
    Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Мoscow: Novaya Volna, 2002.Google Scholar
  2. 2.
    Kas’yan, L.I. and Pal’chikov, V.A., Russ. J. Org. Chem., 2010, vol. 46, no. 1, p. 1. doi 10.1134/S107042801001001XCrossRefGoogle Scholar
  3. 3.
    Bergmeier, S.C., Tetrahedron, 2000, vol. 56, no. 17, p. 2561. doi 10.1016/S0040-4020(00)00149-6CrossRefGoogle Scholar
  4. 4.
    Inaba, T., Yamada, Y., Abe, H., Sagawa, S., and Cho, H., J. Org. Chem., 2000, vol. 65, no. 6, p. 1623. doi 10.10201/jo991793eCrossRefGoogle Scholar
  5. 5.
    Cabanel-Duvillard, I., Berier, J.F., Royer, J., and Husson, H.P., Tetrahedron Lett., 1998, vol. 39, no. 29, p. 5181. doi 10.1016/S0040-4039(98)01017-XCrossRefGoogle Scholar
  6. 6.
    Soumyanarayanan, U., Bhat, V.G., Kar, S.S., and Mathew, J.A., Org. Med. Chem. Lett., 2012, no. 1, p. 23. doi 10.1186/2191-2858CrossRefGoogle Scholar
  7. 7.
    Sadygov, O.A., Alimardanov, Kh.M., and Abbasov, M.F., Russ. J. Gen. Chem., 2009, vol. 79, no. 8, p. 1698. doi 10.1134/S107036320908 0192CrossRefGoogle Scholar
  8. 8.
    Veliev, M.G., Sadygov, O.A., Alimardanov, Kh.M., and Shatirova, M.I., Russ. J. Org. Chem., 2007, vol. 43, no. 11, p. 1604. doi 10.1134/S1070428007110036CrossRefGoogle Scholar
  9. 9.
    Veliev, M.G., Sadygov, O.A., Shatirova, M.I., and Alimardanov, Kh.M., Russ. J. Org. Chem., 2008, vol. 44, no. 9, p. 1282. doi 10.1134/S10-70428008090066CrossRefGoogle Scholar
  10. 10.
    Dobroserdova, I.B. and Anisimov, A.B., Praktikum po neftekhimicheskomu sintezu (Workshop on Petrochemical Synthesis), Moscow: Mosk. Gos. Univ., 1981.Google Scholar
  11. 11.
    Babko, A.K. and Pyatnitskii, I.V., Kolichestvennyi analiz (Quantitative Analysis), Moscow: Vysshaya Shkola, 1962.Google Scholar
  12. 12.
    Colthup, N.B., Daly, L.H., and Wiberley, S.E., Introduction to Infrared and Raman Spectroscopy, Boston: Elsevier, Academic Press, 1990.Google Scholar
  13. 13.
    Derome, A.E., Modern NMR Techniques for Chemical Research, New York: Pergamon Press, 1987.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • O. A. Sadygov
    • 1
  • Kh. M. Alimardanov
    • 1
  • Sh. I. Ismailova
    • 1
  • N. R. Babaev
    • 1
  1. 1.Mammadaliyev Institute of Petrochemical ProcessesAzerbaijan National Academy of SciencesBakuAzerbaijan

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