Skip to main content
SpringerLink
Log in

Electrochemical behaviour of aldehyde-N-arylhydrazones at platinum electrode and their characterization

  • Published:
Russian Journal of Electrochemistry Aims and scope Submit manuscript

Abstract

A series of chemically and pharmaceutically interesting 2,5-disubstituted-1,3,4-oxadiazoles were efficiently synthesized from the anodic oxidation of aldehyde-N-arylhydrazones at platinum anode by using NaClO4 as supporting electrolyte in MeOH solution under controlled potential electrolysis at room temperature. The products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The salient features of this protocol are mild reaction conditions, short reaction time, accelerated rate, high yield and simple work-up procedure.

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. Jin, Z., Nat. Prod. Rep., 2003, vol. 20, p. 584.

    Article  CAS  Google Scholar 

  2. Ghirian, D., Schwatz, I., and Simiti, I., Farmacia, 1974, vol. 22, p. 141.

    Google Scholar 

  3. Dolman, S.J., Gosselin, F., O’Shea, P.D., and Davies, I.W., J. Org. Chem., 2006, vol. 71, p. 9548.

    Article  CAS  Google Scholar 

  4. Zheng, X., Li, Z., Wang, Y., Chen, W., Huang, Q., Liu, C., and Song, G., J. Fluorine Chem., 2003, vol. 123, p. 163.

    Article  CAS  Google Scholar 

  5. Zou, X.J., Lai, L.H., Jin, G.Y., and Zhang, Z.X., J. Agric. Food Chem., 2002, vol. 50, p. 3757.

    Article  CAS  Google Scholar 

  6. Wolkenberg, S.E. and Boger, D.L., J. Org. Chem., 2002, vol. 67, p. 7361.

    Article  CAS  Google Scholar 

  7. Mashraqui, S.H., Ghadigaonkar, S.G., and Kenny, R.S., Synth. Commun., 2003, vol. 33, p. 2541.

    Article  CAS  Google Scholar 

  8. Wang, X.C., Li, Z., Wei, B.G., and Yang, J.Y., Synth. Commun., 2002, vol. 32, p. 1097.

    Article  CAS  Google Scholar 

  9. Dabiri, M., Salehi, P., Baghbanzadeh, M., and Bahramnejad, M., Tetrahedron Lett., 2006, vol. 47, p. 6983.

    Article  CAS  Google Scholar 

  10. Rostamizadeh, S. and Housaini, S.A.G., Tetrahedron Lett., 2004, vol. 45, p. 8753.

    Article  CAS  Google Scholar 

  11. Tandon, V.K. and Chhor, R.B., Synth. Commun., 2001, vol. 31, p. 1727.

    Article  CAS  Google Scholar 

  12. Diana, G.D., Volkots, D.L., Nitz, T.J., Biailly, T.R., Long, M.A., Vesico, N., Aldous, A., Pevear, D.C., and Dukto, F.J., J. Med. Chem., 1994, vol. 37, p. 2421.

    Article  CAS  Google Scholar 

  13. Liras, S., Allen, M.P., and Segelstein, B.E., Synth. Commun., 2000, vol. 30, p. 437.

    Article  CAS  Google Scholar 

  14. Carlsen, H.J. and Jorgensen, K.B., J. Heterocycl. Chem., 1994, vol. 31, p. 805.

    Article  CAS  Google Scholar 

  15. Tully, W.R., Cardner, C.R., Gillespi, R.J., and Westwood, R., J. Med. Chem., 1991, vol. 34, p. 2060.

    Article  CAS  Google Scholar 

  16. Klingsberg, E., J. Am. Chem. Soc., 1958, vol. 80, p. 5786.

    Article  CAS  Google Scholar 

  17. Kerr, N.V., Ott, D.G., and Hayes, F.N., J. Am. Chem. Soc., 1960, vol. 82, p. 186.

    Article  CAS  Google Scholar 

  18. Short, F.W. and Long, F.M., J. Heterocycl. Chem., 1969, vol. 6, p. 707.

    Article  CAS  Google Scholar 

  19. Brain, C.T., Paul, J.M., Loong, Y., and Oakley, P.J., Tetrahedron Lett., 1999, vol. 40, p. 3275.

    Article  CAS  Google Scholar 

  20. Brain, C.T. and Brunton, S.A., Synlett, 2001, vol. 3, p. 382.

    Google Scholar 

  21. Dabiri, M., Salehi, P., Baghbanzadeh, M., Zolfigol, M.A., and Bahramnejad, M., Synth. Commun., 2007, vol. 37, p. 1201.

    Article  CAS  Google Scholar 

  22. Polshettiwar, V. and Varma, R.S., Tetrahedron Lett., 2008, vol. 49, p. 879.

    Article  CAS  Google Scholar 

  23. Fry, A.J., Synthetic Organic Electrochemistry, Wiley: New York, 1989.

    Google Scholar 

  24. Shono, T., Electroorganic Synthesis, Academic Press Ltd: London, 1991.

    Google Scholar 

  25. Shang, Z., Synth. Commun., 2006, vol. 36, p. 2927.

    Article  CAS  Google Scholar 

  26. Jedlovska, E. and Lesko, J., Synth. Commun., 1994, vol. 24, p. 1879.

    Article  CAS  Google Scholar 

  27. Torii, S., Electroorganic Reduction Synthesis, Kodansha: Tokyo, 2006.

    Google Scholar 

  28. Lund, H. and Hammerich, O., Organic Electrochemistry, Marcel Dekker: New York, 2001.

    Google Scholar 

  29. Little, R.D. and Weinberg, N.L., Electroorganic Synthesis, Marcel Dekker: New York, 1991.

    Google Scholar 

  30. Hoormann, D., Jorissen, J., and Putter, H., Chem. Ing. Tech., 2005, vol. 77, p. 1363.

    Article  CAS  Google Scholar 

  31. Yoshida, J.I., Kataoka, K., Horcajada, R., and Nagaki, A., Chem. Rev., 2008, vol. 108, p. 2265.

    Article  CAS  Google Scholar 

  32. Barjau, J., Konigs, P., Kataeva, O., and Waldvogel, S.R., Synlett, 2008, vol. 15, p. 2309.

    Google Scholar 

  33. Xu, H.C., Brandt, J.D., and Moeller, K.D., Tetrahedron Lett., 2008, vol. 49, p. 3868.

    Article  CAS  Google Scholar 

  34. Tang, F., Chen, C., and Moeller, K.D., Synthesis, 2007, vol. 21, p. 3411.

    Google Scholar 

  35. Lund, H. and Baizer, M.M., Organic Electrochemistry: An Introduction and a Guide, Marcel Dekker: New York, 1991.

    Google Scholar 

  36. Kyriacou, D.K., Basics of Electroorganic Synthesis, John Wiley & Sons: New York, 1981.

    Google Scholar 

  37. Utley, J., Chem. Soc. Rev., 1997, vol. 26, p. 157.

    Article  CAS  Google Scholar 

  38. Genders, J.D. and Pletcher, D., Chem. Ind., 1996, vol. 18, p. 682.

    Google Scholar 

  39. Utley, J., Chem. Ind., 1994, vol. 6, p. 215.

    Google Scholar 

  40. Sharma, L.K., Singh, S., and Singh, R.K.P., J. Ind. Chem. Soc., 2011, vol. 88, p. 155.

    CAS  Google Scholar 

  41. Sharma, L.K., Singh, S., and Singh, R.K.P., Ind. J. Chem., 2011, vol. 50B, p. 110.

    CAS  Google Scholar 

  42. Singh, S., Kumar, S., Sharma, L.K., and Singh, R.K.P., J. Ind. Chem. Soc., 2009, vol. 86, p. 734.

    CAS  Google Scholar 

  43. Sharma, L.K., Kumar, S., Singh, S., and Singh, R.K.P., Electrokhimiya, 2010, vol. 46, p. 37.

    Google Scholar 

  44. Singh. S., Sharma, L.K., Saraswat, A., and Singh, R.K.P., Montash Chem., 2012 DOI 10.1007/s00706-011-0711-3.

    Google Scholar 

  45. Saraswat, A., Sharma, L. K., Singh, S., Siddiqui, I. R., and Singh, R.K.P., Res. Chem. Intermed., 2012 DOI10.1007/s11164-012-0695-6.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Electrochemical Laboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad, 211 002, India

    Sushma Singh, Laxmi Kant Sharma, Apoorv Saraswat, Ibadur Rahman Siddiqui & Rana Krishna Pal Singh

Authors
  1. Sushma Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Laxmi Kant Sharma
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Apoorv Saraswat
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ibadur Rahman Siddiqui
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rana Krishna Pal Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rana Krishna Pal Singh.

Additional information

Published in Russian in Elektrokhimiya, 2014, Vol. 50, No. 9, pp. 924–931.

The article is published in the original.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Singh, S., Sharma, L.K., Saraswat, A. et al. Electrochemical behaviour of aldehyde-N-arylhydrazones at platinum electrode and their characterization. Russ J Electrochem 50, 831–837 (2014). https://doi.org/10.1134/S1023193514090092

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1023193514090092

Keywords

Search

Navigation