Skip to main content
Log in

Nitropyridines: III. Synthesis of meta-terphenyls by recyclization of nitropyridinium salts

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

Abstract

A two-component Hantzsch synthesis was applied to preparation of nitropyridines and their quaternary salts from various enamines and chalcones based on nitroacetophenone. The recyclization of nitropyridinium quaternary salts under the treatment with an aqueous-alcoholic alkali led to preparation of 5′-methylamino-2′-nitro-m-terphenyl derivatives.

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. Shkil’, G.P., Berdovich, L.V., Lusis, V., Mutsenietse, D., and Sagitullin, R.S., Khim. Geterotsikl. Soedin., 1995, p. 86.

  2. Sagitullina, G.P., Glizdinskaya, L.V., and Sagitullin, R.S., Khim. Geterotsikl. Soedin., 2005, p. 633.

  3. Zimmermann, T., J. Prakt. Chem., 1993, vol. 335, p. 644.

    Article  CAS  Google Scholar 

  4. Zimmermann, T. and Fischer, G.W., J. Prakt. Chem., 1988, vol. 330, p. 35.

    Article  CAS  Google Scholar 

  5. Van der Plas, H.C. and Barczynski, P., Rec. Trav. Chim, Pays-Bas, 1978, vol. 97, p. 256.

    Google Scholar 

  6. Sadek, K.U., Selim, M.A., and Abdel-Motaleb, R.M., Bull. Chem. Soc. Jpn., 1990, vol. 63, p. 652.

    Article  CAS  Google Scholar 

  7. Ivanov, C. and Tcholakova, T., Synthesis, 1981, p. 392.

  8. Eichinger, K., Nussbaumer, P., Balkan, S., and Schulz, G., Synthesis, 1987, p. 1061.

  9. Lee, E., Hur, C.U., Rhee, Y.H., Park, Y.C., and Kim, S.Y., J. Chem. Soc., Chem. Commun., 1993, p. 1466.

  10. Mitsudo, T., Naruse, H., Kondo, T., Ozaki, Y., and Watanabe, Y., Angew. Chem., 1994, vol. 106, p. 595.

    CAS  Google Scholar 

  11. Haglund, O., Hai, A.A.K.M., and Nillson, M., Synthesis, 1990, p. 942.

  12. Arumugam, N. and Kumaraswamy, A., Synthesis, 1981, p. 367.

  13. Domer, F.R., Chihal, D.M., Charles, H.C., and Koch, R.C., J. Med. Chem., 1980, vol. 23, p. 541.

    Article  CAS  Google Scholar 

  14. Markovas, A. and LaMontagne, M.P., J. Med. Chem., 1980, vol. 23, p. 1198.

    Article  Google Scholar 

  15. Li, J.J., Norton, M.B., Reinhard, E.J., Anderson, G.D., Gregory, S.A., Isakson, P.C., Koboldt, C.M., Masferrer, J.L., Perkins, W.E., Seibert, K., Zhang, Y., Zweifel, B.S., and Reitz, D.B., J. Med. Chem., 1996, vol. 39, p. 1846.

    Article  CAS  Google Scholar 

  16. Chavatte, P., Yous, S., Marot, C., Baurin, N., and Lesieur, D., J. Med. Chem., 2001, vol. 44, p. 3223.

    Article  CAS  Google Scholar 

  17. Sagitullina, G.P., Glizdinskaya, L.V., Sitnikov, G.V., and Sagitullin, R.S., Khim. Geterotsikl. Soedin., 2002, p. 1518.

  18. Sagitullina, G.P., Glizdinskaya, L.V., Oleinikova, S.I., Atavin, E.G., and Sagitullin, R.S., Zh. Org. Khim., 2005, vol. 41, p. 1395.

    Google Scholar 

  19. Ciller, J.A., Seoane, C., Soto, J.L. and J. Heterocycl. Chem., 1985, vol. 22, p. 1663.

    Article  CAS  Google Scholar 

  20. Knorr, L., Chem. Ber., 1892, vol. 25, p. 775.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Dedicated to Academician of the Russian Academy of Sciences N.S.Zefirov on occasion of his 70th anniversary

Original Russian Text © G.P. Sagitullina, L.V. Glidzinskaya, R.S. Sagitullin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 8, pp. 1222–1226.

For communication II, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sagitullina, G.P., Glidzinskaya, L.V. & Sagitullin, R.S. Nitropyridines: III. Synthesis of meta-terphenyls by recyclization of nitropyridinium salts. Russ J Org Chem 42, 1203–1207 (2006). https://doi.org/10.1134/S1070428006080173

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428006080173

Keywords

Navigation