Skip to main content
Log in

Synthesis and structure of 2,4-dinitrophenylcyanoacetamide derivatives as CH acids and their organic salts

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

C-Arylation of cyanoacetamides with chloro-2,4-dinitrobenzene was performed in acetonitrile in presence of potassium carbonate. The CH acids obtained react with triethylamine or N-methylmorpholine to give salts that contain anions possessing highly conjugated system of unsaturated bonds.

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. M. Hojatti, K. T. Leffek, Can. J. Chem., 1984, 62, 2653.

    Article  CAS  Google Scholar 

  2. M. Gromova, C. G. Beguin, R. Goumont, N. Faucher, M. Tordeux, F. Terrier, Magn. Reson. Chem., 2000, 38, 655.

    Article  CAS  Google Scholar 

  3. F. Terrier, E. Magnier, E. Kizilian, C. Wakselman, E. Buncel, J. Am. Chem. Soc., 2005, 127, 5563.

    Article  CAS  Google Scholar 

  4. J. Kaválek, V. Macháček, A. Lyčka, V. Čtèrba, Collect. Czech. Chem. Common., 1976, 41, 590.

    Google Scholar 

  5. K. T. Leffek, P. H. Tremaine, Can. J. Chem., 1971, 49, 1979.

    Article  CAS  Google Scholar 

  6. M. Strauss, R. Torres, J. Org. Chem., 1989, 54, 756.

    Article  CAS  Google Scholar 

  7. Yu. G. Gololobov, O. A. Linchenko, P. V. Petrovskii, Z. A. Starikova, I. A. Garbuzova, Heteroatom Chem., 2007, 18, 108.

    Article  CAS  Google Scholar 

  8. Yu. G. Gololobov, O. A. Linchenko, Z. A. Starikova, I. A. Garbuzova, P. V. Petrovskii, Izv. Akad. Nauk, Ser. Khim., 2005, 2393 [Russ. Chem. Bull., Int. Ed., 2005, 54, 2471].

    Google Scholar 

  9. Yu. G. Gololobov, O. A. Linchenko, P. V. Petrovskii, I. A. Garbuzova, V. N. Khrustalev, Izv. Akad. Nauk, Ser. Khim., 2006, 1261 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1309].

    Google Scholar 

  10. Yu. G. Gololobov, O. A. Linchenko, P. V. Petrovskii, V. N. Khrustalev, I. A. Garbuzova, Heteroatom Chem., 2007, 18, 421.

    Article  CAS  Google Scholar 

  11. Yu. G. Gololobov, O. A. Linchenko, P. V. Petrovskii, V. N. Khrustalev, I. A. Garbuzova, Mendeleev Commun., 2007, 17, 232.

    Article  CAS  Google Scholar 

  12. Yu. G. Gololobov, O. V. Dovgan, I. R. Golding, P. V. Petrovskii, I. A. Garbuzova, Heteroatom Chem., 2002, 13, 36.

    Article  CAS  Google Scholar 

  13. Zhi-Sheng Jia, Chen-Ze Qi, Di-Lun Yang, Acta Chim. Sinica, 1996, 54, 521.

    CAS  Google Scholar 

  14. I. V. Fedyanin, K. A. Lyssenko, Z. A. Starikova, M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 2004, 1106 [Russ. Chem. Bull., Int. Ed., 2004, 43, 1153].

    Google Scholar 

  15. A. S. Cieplak, in Structure Correlation, Eds H. B. Bürgi, J. D. Dunitz, Verlag Chemie, Weinheim, 1994, 205.

    Chapter  Google Scholar 

  16. Yu. V. Nelyubina, M. Yu. Antipin, K. A. Lyssenko, J. Phys. Chem. A, 2007, 111, 1091.

    Article  CAS  Google Scholar 

  17. G. M. Sheldrick, SADABS, Bruker AXS Inc., Madison, WI-53719, USA, 1997.

    Google Scholar 

  18. G. M. Sheldrick, SHELXTL PLUS, SHELXTL-97, Version 5.10, Bruker AXS Inc., Madison, WI-53719, USA, 1997.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. G. Gololobov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2365–2370, December, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gololobov, Y.G., Gol’ding, I.R., Terrie, F. et al. Synthesis and structure of 2,4-dinitrophenylcyanoacetamide derivatives as CH acids and their organic salts. Russ Chem Bull 58, 2443–2448 (2009). https://doi.org/10.1007/s11172-009-0342-6

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-009-0342-6

Key words

Navigation