Skip to main content

Aluminum hydrogen sulfate as a green catalyst for the solvent-free synthesis of pyrazolopyridines

Russian Journal of General Chemistry volume 85, pages 1179–1183 (2015)Cite this article

Abstract

Aluminum hydrogen sulfate turned out to be a mild, convenient, and efficient reagent for the conversion of substituted benzyl alcohols into pyrazolopyridines via condensation with 3-methyl-1H-pyrazole-5-amine and CH acid (malononitrile or indan-1,3-dione) at room temperature under solvent-free conditions with high yield, high purity, and short reaction time.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

References

  1. Huang, S., Lin, R., Yu, Y., Connolly, P.J., Chiu, G., Li, S., Emanuel, S.L., and Middleton, A., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 1243.

    CAS  Article  Google Scholar 

  2. Saggar, S.A., Sisko, J.T., Tucker, T.J., Tynebor, R.M., Su, D.S., and Anthony, N.J., US Patent Appl. Publ. no. 2007 021 442.

  3. Zhang, P., Pennell, A.M.K., Wright, J.J.K., Chen, W., Leleti, M.R., Li, Y., Li, L., and Xu, Y., PCT Int. Appl. Publ. no. WO 2007 002 293.

  4. Chiu, G., Li, S., Connelly, P.J., Middleton, S.A., Emanuel, S.L., Huang, S., Lin, R., Lu, Y., PCT Int. Appl. Publ. no. WO 2006130673.

  5. Feurer, A., Luithle, J., Wirtz, S., Koenig, G., Stasch, J., Stahl, E., Schreiber, R., Wunder, F., and Lang, D., PCT Int. Appl. no. WO 2004 009 589.

  6. Hafez, A.A., Awad, I., and Ahmed, R., Collect. Czech. Chem. Commun., 1993, vol. 58, p. 1198.

    Article  Google Scholar 

  7. Trucker, T.J., Sisko, J.T., Tynebor, R.M., Williams, T.M., Felock, P.J., Flynn, J.A., Lai, M.T., Liang, Y., McGaughey, G., Liu, M., Miller, M., Moyer, G., Munshi, V., Poehnelt, R.P., Prasad, S., Reid, J.C., Sanchez, R., Torrent, M., Vacca, J.P., Wan, B.L., and Yan, Y., J. Med. Chem., 2008, vol. 51, p. 6503.

    Article  Google Scholar 

  8. Stein, R.G., Biel, J.H., and Singh, T., J. Med. Chem., 1970, vol. 13, p. 153.

    CAS  Article  Google Scholar 

  9. Straub, A., Benet-Buckoltz, J., Frode, R., Kem, A., Kohlsdorfer, C.M., Schmitt, P., Schwarz, T., Siefert, H.M., and Stasch, J.P., Bioorg. Med. Chem., 2002, vol. 10, p. 1711.

    CAS  Article  Google Scholar 

  10. de Mello, H., Echevarria, A., Bemardino, A.M., Canto-Cavalheiro, M., and Leon, L.L., J. Med. Chem., 2004, vol. 47, p. 5427.

    Article  Google Scholar 

  11. Ochiai, H., Ishida, A., Ohtani, T., Kusumi, K., Kishikawa, K., Yamamoto, S., Takeda, H., Obata, T., Makai, H., and Toda, M., Bioorg. Med. Chem., 2004, vol. 12, p. 4089.

    CAS  Article  Google Scholar 

  12. Bare, T.M., Mclaren, C.D., Campbell, J.B., Firor, J.W., Resch, J.F., Walters, C.P., Salama, A.I., Meiners, B.A., and Patel, J.B., J. Med. Chem., 1989, vol. 32, p. 2561.

    CAS  Article  Google Scholar 

  13. Hoehn, H., Polacek, I., and Schulze, E., J. Med. Chem., 1973, vol. 16, p. 1340.

    CAS  Article  Google Scholar 

  14. Chu, I. and Lynch, B.M., J. Med. Chem., 1975, vol. 18, p. 161.

    CAS  Article  Google Scholar 

  15. Zare, L. and Nikpassand, M., Chin. Chem. Lett., 2011, vol. 22, p. 531.

    CAS  Article  Google Scholar 

  16. Nikpassand, M., Zare, L., and Saberi, M., Monatsh. Chem., 2012, vol. 143, p. 289.

    CAS  Article  Google Scholar 

  17. Nikpassand, M., Zare, L., and Shafaati, T., Chin. J. Chem., 2012, vol. 30, p. 604.

    CAS  Article  Google Scholar 

  18. Nikpassand, M., Zare Fekri, L., Gharib, M., and Marvi, M., Lett. Org. Chem., 2012, vol. 9, p. 745.

    CAS  Article  Google Scholar 

  19. Zare, L., Mahmoodi, N.O., Yahyazadeh, A., and Mamaghani, M., Synth. Commun., 2012, vol. 41, p. 2323.

    Article  Google Scholar 

  20. Nikpassand, M., Mamaghani, M, Shirini, F., and Tabatabaeian, K.A., Ultrason. Sonochem., 2010, vol. 17, p. 301

    CAS  Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran

    M. Nikpassand

  2. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    L. Zare Fekri

Authors
  1. M. Nikpassand
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. Zare Fekri
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Nikpassand.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Nikpassand, M., Zare Fekri, L. Aluminum hydrogen sulfate as a green catalyst for the solvent-free synthesis of pyrazolopyridines. Russ J Gen Chem 85, 1179–1183 (2015). https://doi.org/10.1134/S1070363215050308

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215050308

Keywords

  • pyrazolopyridine
  • solvent free
  • aluminum hydrogen sulfate
  • green catalyst