Russian Journal of Organic Chemistry

, Volume 44, Issue 12, pp 1765–1772 | Cite as

Synthesis and structure of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone imines

  • A. P. Avdeenko
  • S. A. Konovalova
  • A. G. Sergeeva
  • R. I. Zubatyuk
  • G. V. Palamarchuk
  • O. V. Shishkin
Article

Abstract

New N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone imines were synthesized by reaction of isocyanates with the corresponding substituted 4-aminophenols, and their structure was determined on the basis of 1H and 13C NMR spectra and X-ray diffraction data.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Torizuka, M. and Kikugawa, Y., and Nagashima, H., Synthesis, 1986, no. 3, p. 226; Kozyukov, V.P., Orlov, G.I., and Mironov, V.F., Zh. Obshch. Khim., 1981, vol. 51, p. 2017.Google Scholar
  2. 2.
    Bender, C.F. and Widenhoefer, R.A., Org. Lett., 2006, vol. 8, p. 5303; Singh, K., Arora, D., and Singh, S., Tetrahedron Lett., 2006, vol. 47, p. 4205.CrossRefGoogle Scholar
  3. 3.
    Beaver, D.J., Roman, D.P., and Stoffel, P.J., J. Org. Chem., 1959, vol. 24, p. 1676.CrossRefGoogle Scholar
  4. 4.
    Dai, Y., Hartandi, K., Ji, Zh., and Ahmed, A.A., J. Med. Chem., 2007, vol. 50, p. 1584; Vovk, M.V., Bratenko, M.K., Chornous, V.O., Petrenko, V.S., Shvartau, V.V., and Denisenko, O.M., Zh. Org. Farm. Khim., 2006, vol. 4, no. 16, p. 63.CrossRefGoogle Scholar
  5. 5.
    Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Pesticides. Chemistry, Technology, and Applications), Moscow: Khimiya, 1987.Google Scholar
  6. 6.
    Adams, R. and Reifschneider, W., Bull. Soc. Chim. Fr., 1958, no. 25, p. 23; Fujita, S., Synth. Org. Chem. Jpn., 1985, vol. 43, p. 153; Nogami, M., Hishida, T., Yamada, M., Mikawa, H., and Shirota, Y., Bull. Chem. Soc. Jpn., 1975, vol. 48, p. 3709; Engler, T.A., Chai, W., and Lynch, K.O., Tetrahedron Lett., 1995, vol. 36, p. 7003; Heine, H.W., Ciaccio, J.A., Carson, K.G., and Taylor, C.M., J. Org. Chem., 1990, vol. 55, p. 4039; Markava, E.Ya., Liepin’sh, E.E., Freimanis, Ya.F., Gustina, D.V., and Laivin’sh, G.M., Zh. Org. Khim., 1990, vol. 26, p. 1987; Avdeenko, A.P., Russ. J. Org. Chem., 1998, vol. 34, p. 515.Google Scholar
  7. 7.
    Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org. Chem., 2006, vol. 42, p. 349.CrossRefGoogle Scholar
  8. 8.
    Avdeenko, A.P., Konovalova, S.A., Burmistrov, K.S., Toropin, N.V., and Vakulenko, A.V., Russ. J. Org. Chem., 2004, vol. 40, p. 962; Avdeenko, A.P., Marchenko, I.L., and Konovalova, S.A., Russ. J. Org. Chem., 2001, vol. 37, p. 72.CrossRefGoogle Scholar
  9. 9.
    Avdeenko, A.P., Zhukova, S.A., Menafova, Yu.V., and Yusina, A.L., Russ. J. Org. Chem., 2000, vol. 36, p. 808; Avdeenko, A.P. and Menafova, Yu.V., Russ. J. Org. Chem., 2006, vol. 42, p. 403.Google Scholar
  10. 10.
    Avdeenko, A.P., Yusina, A.L., Menafova, Yu.V., and Pirozhenko, V.V., Russ. J. Org. Chem., 1995, vol. 31, p. 1386; Avdeenko, A.P. and Marchenko, I.L., Russ. J. Org. Chem., 2001, vol. 37, p. 1587.Google Scholar
  11. 11.
    Petersen, S., Gauss, W., and Urdschaft, E., Angew. Chem., 1955, vol. 67, p. 217.CrossRefGoogle Scholar
  12. 12.
    Anticancer Molecules. Structure, Function, and Design, Maruta, H., Ed. (Annals of the New York Academy of Sciences, 1999, vol. 886, p. 280); Golubeva, I.S., Kubasova, I.K., Glibin, E.N., and Popova, E.B., Khim.-Farm. Zh., 2000, vol. 34, p. 3.Google Scholar
  13. 13.
    Fieser, L.F. and Fieser, M., Advanced Organic Chemistry, New York: Reinhold, 1961.Google Scholar
  14. 14.
    Burmistrov, K.S., Doctoral (Chem.) Dissertation, Dnepropetrovsk, 1990.Google Scholar
  15. 15.
    Avdeenko, A.P., Pirozhenko, V.V., Yagupol’skii, L.M., and Marchenko, I.L., Russ. J. Org. Chem., 2001, vol. 37, p. 991.CrossRefGoogle Scholar
  16. 16.
    Pirozhenko, V.V. and Avdeenko, A.P., Russ. J. Org. Chem., 1995, vol. 31, p. 1514.Google Scholar
  17. 17.
    Avdeenko, A.P., Konovalova, S.A., and Ludchenko, O.N., Vopr. Khim. Khim. Tekhnol., 2006, no. 6, p. 36.Google Scholar
  18. 18.
    Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989, vol. 58, p. 713.Google Scholar
  19. 19.
    Sheldrick, G.M., SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data. Rev. 5.1, 1998; Burgi, H.-B. and Dunitz, J.D., Structure Correlation, Weinheim: VCH, 1994, vol. 2., p. 741.Google Scholar
  20. 20.
    Gorbatenko, V.I., Zhuravlev, E.Z., and Samarai, L.I., Izotsianaty. Metody sinteza i fiziko-khimicheskie svoi- stva alkil-, aril- i geterotsiklicheskikh izotsianatov (Isocyanates. Methods of Synthesis and Physicochemical Properties of Alkyl, Aryl, and Heterocyclic Isocyanates), Kiev: Naukova Dumka, 1987, pp. 17, 30; The Chemistry of Cyanates and Their Thio Derivatives, Patai, S., Ed., Chichester: Wiley, 1977, vol. 2.Google Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • A. P. Avdeenko
    • 1
  • S. A. Konovalova
    • 1
  • A. G. Sergeeva
    • 1
  • R. I. Zubatyuk
    • 2
  • G. V. Palamarchuk
    • 2
  • O. V. Shishkin
    • 2
  1. 1.Donbass State Machine-Building AcademyKramatorskUkraine
  2. 2.Institute of Single CrystalsNational Academy of Sciences of UkraineKhar’kovUkraine

Personalised recommendations