Skip to main content
Log in

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

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  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.

  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.

    Article  CAS  Google Scholar 

  3. Beaver, D.J., Roman, D.P., and Stoffel, P.J., J. Org. Chem., 1959, vol. 24, p. 1676.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  5. Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Pesticides. Chemistry, Technology, and Applications), Moscow: Khimiya, 1987.

    Google Scholar 

  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.

  7. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org. Chem., 2006, vol. 42, p. 349.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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. Petersen, S., Gauss, W., and Urdschaft, E., Angew. Chem., 1955, vol. 67, p. 217.

    Article  CAS  Google Scholar 

  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.

  13. Fieser, L.F. and Fieser, M., Advanced Organic Chemistry, New York: Reinhold, 1961.

    Google Scholar 

  14. Burmistrov, K.S., Doctoral (Chem.) Dissertation, Dnepropetrovsk, 1990.

  15. Avdeenko, A.P., Pirozhenko, V.V., Yagupol’skii, L.M., and Marchenko, I.L., Russ. J. Org. Chem., 2001, vol. 37, p. 991.

    Article  CAS  Google Scholar 

  16. Pirozhenko, V.V. and Avdeenko, A.P., Russ. J. Org. Chem., 1995, vol. 31, p. 1514.

    Google Scholar 

  17. Avdeenko, A.P., Konovalova, S.A., and Ludchenko, O.N., Vopr. Khim. Khim. Tekhnol., 2006, no. 6, p. 36.

  18. Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989, vol. 58, p. 713.

    CAS  Google Scholar 

  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.

  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 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. P. Avdeenko.

Additional information

Original Russian Text © A.P. Avdeenko, S.A. Konovalova, A.G. Sergeeva, R.I. Zubatyuk, G.V. Palamarchuk, O.V. Shishkin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 12, pp. 1791–1798.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Avdeenko, A.P., Konovalova, S.A., Sergeeva, A.G. et al. Synthesis and structure of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone imines. Russ J Org Chem 44, 1765–1772 (2008). https://doi.org/10.1134/S1070428008120075

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008120075

Keywords

Navigation