Skip to main content
SpringerLink
Log in

α-aminoazoles in synthesis of heterocycles: IV. Regiodirection of 3(5)-amino-5(3)-methylpyrazole reaction with hexafluoroacetylacetone

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

Abstract

The reaction of 3(5)-amino-5(3)-methylpyrazole with hexafluoroacetylacetone depending on the process conditions led to the formation either of pyrazolo[1,5-a]pyrimidine or pyrazolo[3,4-b]-pyridine. By means of 2D NMR spectroscopy the structure was established of a stable intermediate product, 2-methyl-5,7-bis(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]-pyrimidine-5,7-diol, whose dehydration yielded the above compounds.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Emelina, E.E., Petrov, A.A., Selivanov, S.I., and Filyukov, D.V., Zh. Org. Khim., 2008, vol. 44, p. 259.

    Google Scholar 

  2. Abu, Almaati, T.M. and El-Taweel, F. M., J. Heterocycl. Chem., 2004, vol. 41, p. 109.

    Article  Google Scholar 

  3. Sellery, S., Gratteri, P., Costagli, C., Bonaccini, C., Coztanzo, A., Melani, F., Guerrini, G., Ciciani, G., Costa, B., Spinetti, F., Martini, C., and Bruni, F., Bioorg. Med. Chem., 2005, vol. 13, p. 4821; Gopalsamy, A., Yang, H., Ellingboe, J.W., Tsou, H.-R., Zhang, N., Honores, E., Powell, D., Miranda, M., McGinnis, J.P., and Rabindran, S.K., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 1591; Makarov, V.A., Riabova, O.B., Granik, V.G., Dahse, H.-M., Stelzner, A., Wutzler, P., and Schmidtke, M., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 37; Thominiaux, C., Dolle, F., James, M.L., Bramoulle, Y., Boutin, H., Besret, L., Gregoire, M.-C., Valette, H., Bottlaender, M., Tavitian, B., Hantraye, Ph., Selleri, S., and Kassiou, M., Appl. Rad. Isotopes., 2006, vol. 64, p. 570.

    Article  Google Scholar 

  4. George, C.F.P., Lancet. 2001, vol. 357, p. 1623.

    Article  Google Scholar 

  5. Petrov, A.A., Emelina, E.E., and Firsov, A.V., Zh. Org. Khim., 2001, vol. 37, p. 899.

    Google Scholar 

  6. Emelina, E.E., Petrov, A.A., and Firsov, A.V., Zh. Org. Khim., 2003, vol. 39, p. 299.

    Google Scholar 

  7. Kolehmainen, E., Laihia, K., Firsov, A., Zayzev, V., Petrov, A.A., and Emelina, E.E. Magn. Res. Chem., 2002, vol. 40, p. 480.

    Article  CAS  Google Scholar 

  8. Dalinger, I.L., Vatsadse, I.A., and Shevelev, S.A., J. Comb. Chem., 2005, vol. 7, p. 236.

    Article  CAS  Google Scholar 

  9. Balicki, R., Pol. J. Chem., 1983, vol. 57, p. 1251; Balicki, R., Pol. J. Chem., 1982, vol. 56, p. 1125.

    CAS  Google Scholar 

  10. Kirkpatrik, W.E., Okabe, T., Hillard, I.W., Robins, R.K., Dren, A.T., and Novinson, Th., J. Med. Chem., 1977, vol. 20, p. 386.

    Article  Google Scholar 

  11. Nam, N.L., Grandberg, I.I., and Sorokin, V.I., Khim. Geterotsikl. Soedin., 2002, vol. 38, p. 1555.

    Google Scholar 

  12. Balicki, R., Pol. J. Chem., 1981, vol. 55, p. 1995.

    CAS  Google Scholar 

  13. Piantini, U., Sorensen, O.W., and Ernst, R.R., J. Am. Chem. Soc., 1982, vol. 104, p. 6800.

    Article  CAS  Google Scholar 

  14. Aue, W.P., Karhan, J., and Ernst, R.R., J. Chem. Phys., 1976, vol. 64, p. 4226.

    Article  CAS  Google Scholar 

  15. Jeener, J., Meier, G.H., Bachman, P., and Ernst, R.R., J. Chem. Phys., 1979, vol. 71, p. 4546.

    Article  CAS  Google Scholar 

  16. Bodenhausen, G. and Ruben, D.J., Chem. Phys. Lett., 1980, vol. 69, p. 185.

    Article  CAS  Google Scholar 

  17. Traficante, D.D. and Meadows, M.D., Concepts Magn. Res., 1997, vol. 9, p. 359.

    Article  CAS  Google Scholar 

  18. Tormena, C.F., Freitas, M.P., Rittner, R., and Abraham, R.J.A., Magn. Res. Chem., 2002, vol. 40, p. 279.

    Article  CAS  Google Scholar 

  19. Potapov, V.M., Stereokhimiya (Stereochemistry), Moscow: Khimiya, 1988, 464 p.

    Google Scholar 

  20. Sauer, S.P.A. and Krivdin, L.B., Magn. Res. Chem., 2004, vol. 42, p. 671.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 198504, Russia

    A. A. Petrov, E. E. Emelina & S. I. Selivanov

Authors
  1. A. A. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. E. Emelina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. I. Selivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Petrov.

Additional information

Original Russian Text © A.A. Petrov, E.E. Emelina, S.I. Selivanov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 269–275.

For communication III, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Petrov, A.A., Emelina, E.E. & Selivanov, S.I. α-aminoazoles in synthesis of heterocycles: IV. Regiodirection of 3(5)-amino-5(3)-methylpyrazole reaction with hexafluoroacetylacetone. Russ J Org Chem 44, 263–269 (2008). https://doi.org/10.1134/S1070428008020139

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008020139

Keywords

Search

Navigation