Skip to main content
SpringerLink
Log in

Synthesis of ditopic ligands containing bis(1H-pyrazol-1-yl)-methane fragments

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

Abstract

New approaches have been proposed for the synthesis of compounds containing two bis(1H-pyrazol-1-yl)methane fragments. Nucleophilic replacement of the halogen atoms in appropriate tetrabromo derivatives by pyrazoles in the superbasic system KOH-DMSO gave ditopic chelating ligands: 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane, 1,4-bis[bis(1H-pyrazol-1-yl)methyl]benzene, and 1,4-bis[bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl]benzene. 1,4-Bis[bis(1H-pyrazol-1-yl)methyl]benzene was also synthesized by reaction of 1H-pyrazole with terephthalaldehyde in the presence of thionyl chloride. 1,1,2,2-Tetrakis(1H-pyrazol-1-yl)ethane was converted into the corresponding tetraiodo and tetranitro derivatives.

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. Pettinari, C. and Pettinari, R., Coord. Chem. Rev., 2005, vol. 249, p. 663.

    Article  CAS  Google Scholar 

  2. Reger, D.L., Watson, R.P., Smith, M.D., and Pellechia, P.J., Organometallics, 2005, vol. 24, p. 1544.

    Article  CAS  Google Scholar 

  3. Reger, D.L., Watson, R.P., Smith, M.D., and Pellechia, P.J., Organometallics, 2006, vol. 25, p. 743.

    Article  CAS  Google Scholar 

  4. Reger, D.L., Semeniuc, R.F., and Smith, M.D., Dalton Trans., 2002, p. 476; Reger, D.L., Semeniuc, R.F., and Smith, M.D., J. Organomet. Chem., 2003, vol. 666, p. 87; Reger, D.L., Brown, K.J., Gardinier, J.R., and Smith, M.D., J. Organomet. Chem., 2005, pp. 690, 1889; Robin, A. and Fromm, K., Coord. Chem. Rev., 2006, vol. 250, p. 2127.

  5. Reger, D.L., Semeniuc, R.F., and Smith, M.D., Dalton Trans., 2003, p. 285; Reger, D.L., Watson, R.P., Gardinier, J.R., and Smith, M.D., Inorg. Chem., 2004, vol. 43, p. 6609; Reger, D.L., Gardinier, J.R., Grattan, T.C., Smith, M.R., and Smith, M.D., New J. Chem., 2003, vol. 27, p. 1670.

  6. Reger, D.L., Gardinier, J.R., Grattan, T.C., and Smith, M.D., Polyhedron, 2004, vol. 23, p. 291.

    Article  CAS  Google Scholar 

  7. Katritzky, A.R., Kuzmierkiewicz, W., Rachwal, B., Rachwal, S., and Thomson, J., J. Chem. Soc., Perkin Trans. 1, 1987, p. 811.

  8. Schmidt, T. and Rudolf, T., Eur. Patent no. 0008056 B1, 1978.

  9. Khlebnikov, A.I., Anfinogenov, V.A., Rybal’chenko, T.A., and Filimonov, V.D., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1996, vol. 39, nos. 1–2, p. 31.

    CAS  Google Scholar 

  10. Ozeryanskii, V.A. and Pozharskii, A.F., Izv. Ross. Akad. Nauk, Ser. Khim., 2003, p. 257.

  11. Potapov, A.S. and Khlebnikov, A.I., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2003, vol. 46, no. 7, p. 66.

    CAS  Google Scholar 

  12. Vasilevskii, S.F. and Shvartsberg, M.S., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, p. 1071.

  13. Potapov, A.S., Khlebnikov, A.I., and Vasilevskii, S.F., Russ. J. Org. Chem., 2006, vol. 42, p. 1368.

    Article  CAS  Google Scholar 

  14. Claramunt, R.M., Hernandez, H., Elguero, J., and Julia, S., Bull. Soc. Chim. Fr., 1983, p. 5.

  15. Snell, J.M. and Weissberger, A., Org. Synth., 1940, vol. 20, p. 92.

    CAS  Google Scholar 

  16. HyperChem Computational Chemistry: Molecular Visualization and Simulation (release 7 for Windows), Hypercube, 2002.

Download references

Author information

Authors and Affiliations

  1. Polzunov Altai State Technical University, pr. Lenina 46, Barnaul, 656038, Russia

    E. A. Nudnova, A. S. Potapov & A. I. Khlebnikov

  2. Institute of Petroleum Chemistry, Siberian Division, Russian Academy of Sciences, Akademicheskii pr. 3, Tomsk, 634021, Russia

    V. D. Ogorodnikov

Authors
  1. E. A. Nudnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Potapov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Khlebnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. D. Ogorodnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. I. Khlebnikov.

Additional information

Original Russian Text © E.A. Nudnova, A.S. Potapov, A.I. Khlebnikov, V.D. Ogorodnikov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1698–1702.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nudnova, E.A., Potapov, A.S., Khlebnikov, A.I. et al. Synthesis of ditopic ligands containing bis(1H-pyrazol-1-yl)-methane fragments. Russ J Org Chem 43, 1698–1702 (2007). https://doi.org/10.1134/S1070428007110188

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007110188

Search

Navigation