Advertisement

Russian Journal of Organic Chemistry

, Volume 51, Issue 12, pp 1733–1738 | Cite as

Transformations of 2-alkylamino-1,4-naphthoquinones under the action of nitrating mixture in acetic acid

  • L. M. Gornostaev
  • E. V. Nuretdinova
  • T. I. Lavrikova
  • Yu. G. Khalyavina
  • I. S. Kryukovskaya
  • Yu. V. Gatilov
Article
  • 39 Downloads

Abstract

Reactions of 2-alkylamino-1,4-naphthoquinones with a nitrating mixture in acetic acid afforded 2-alkyl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones.

Keywords

Naphthoquinone Naphtho Dimethyl Sulfate Nitrate Mixture Imidazolium Chloride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Hoover, J.R.E. and Day, A.R., J. Am. Chem. Soc., 1954, vol. 76. p. 4148.CrossRefGoogle Scholar
  2. 2.
    Kuo, S.-C., Ibuka, T., Huang, L.-J., Lien, J.-C., Yean, S.-R., Huang, S.-C., Lednicer, D., Morris-Natschke, S., and Lee, K.-H., J. Med. Chem., 1996, vol. 39. p. 1447.CrossRefGoogle Scholar
  3. 3.
    Manivannan, R., Satheshkumar, A., and Elango, K.P., New J. Chem., 2013, vol. 37. p. 3152.CrossRefGoogle Scholar
  4. 4.
    Kuznetsov, V.S. and Efros, L.S., Zh. Org. Khim., 1965, vol. 1. p. 1458.Google Scholar
  5. 5.
    Aly, A.A., Hassan, A.A., Brown, A.B., El-Shaieb, K.M., and Bedaira, T.M.I., J. Heterocycl. Chem., 2011, vol. 48. p. 787.CrossRefGoogle Scholar
  6. 6.
    Aly, A.A., Ishak, E.A., Alsharari, M.A., and Al-Muaikel, N.S.T., J. Heterocycl. Chem., 2012, vol. 49. p. 9.CrossRefGoogle Scholar
  7. 7.
    Gornostaev, L.M., Vigant, M.V., Kargina, O.I., Kuznetsova, A.S., Khalyavina, Yu.G., and Lavrikova, T.I., Russ. J. Org. Chem., 2013, vol. 49. p. 1354.CrossRefGoogle Scholar
  8. 8.
    Gornostaev, L.M., Kryukovskaya, I.S., Lavrikova, T.I., Vigant, M.V., and Gatilov, Yu.V., Russ. J. Org. Chem., 2014, vol. 50. p. 205.CrossRefGoogle Scholar
  9. 9.
    Gornostaev, L.M., Khalyavina, Yu.G., Lavrikova, T.I., Gatilov, Yu.V., Stashina, G.A., and Firgang, S.I., Russ. J. Org. Chem., 2014, vol. 50. p. 1814.CrossRefGoogle Scholar
  10. 10.
    Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2. 1987, no. 12. p. S1–S19.CrossRefGoogle Scholar
  11. 11.
    Sanderson, M.D., Kamplain, J.W., and Bielawski, C.W., J. Am. Chem. Soc., 2006, vol. 128, p. 16514.CrossRefGoogle Scholar
  12. 12.
    Bowser, T.E., Bartlett, V.J., Grier, M.C., Verma, A.K., Warchol, T., Levy, S.B., and Alekshun, M.N., Bioorg. Med. Chem. Lett., 2007, vol. 17. p. 5652.CrossRefGoogle Scholar
  13. 13.
    Kim, O.K., Garrity-Ryan, L.K., Bartlett, V.J., Grier, M.C., Verma, A.K., Medjanis, G., Donatelli, J.E., Macone, A.B., Tanaka, S.K., Levy, S.B., and Alekshun, M.N., J. Med. Chem., 2009, vol. 52. p. 5626.CrossRefGoogle Scholar
  14. 14.
    Belyakov, P.A., Kadentsev, V.I., Chizhov, A.O., Kolotyrkina, N.G., Shashkov, A.S., and Ananikov, V.P., Mendeleev Commun., 2010, vol. 20. p. 125.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  • L. M. Gornostaev
    • 1
  • E. V. Nuretdinova
    • 1
  • T. I. Lavrikova
    • 1
  • Yu. G. Khalyavina
    • 1
  • I. S. Kryukovskaya
    • 2
  • Yu. V. Gatilov
    • 3
    • 4
  1. 1.Astaf’ev Krasnoyarsk State Pedagogical UniversityKrasnoyarskRussia
  2. 2.Voino-Yasenetskii Krasnoyarsk State Medical UniversityKrasnoyarskRussia
  3. 3.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia
  4. 4.Novosibirsk State UniversityNovosibirskRussia

Personalised recommendations