Synthesis of Some 2-Amino-5-Substituted-1,3,4-Oxadiazoles Through the Electrooxidation of Semicarbazone

세미카바존의 전기적 산화에 의한 2-Amino-5-Substituted-1,3,4-Oxadiazoles 합성

  • Kumar, Sanjeev
  • Published : 2009.04.20


The synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles 4 were carried out from the electrooxidation of semicarbazone 3 at the platinum electrode under controlled potential electrolysis in an undivided cell. This is an environmentally benign method in the field of synthetic organic chemistry. The non-aqueous solvents acetic acid and acetonitrile and a supporting electrolyte lithium perchlorate were used for the electrolysis in the electrooxidation. The products were structurally charecterised by IR, $^1H$-NMR, $^{13}C$-NMR and elemental analysis.


Electrooxidation;Constant potential;Electrolysis;Electrolyte;Oxadiazole;Semicarbazone;Platinum electrode;Green chemistry


  1. Holla, B. S.; Gonaslaves, R.; Shenoy, S. Eur. J.Med. Chem. 2000, 35, 267
  2. Cesur, N.; Birteksoz, S.; Otuk, G. Acta. Pharm. Turcica 2002, 44, 23
  3. Laddi, U. V.; Desai, S. R.; Bennur, R. S.; Bennur, S. C. Indian J. Heterocycl. Chem. 2002, 11, 319.
  4. Zou, X. Z.; Zhang, Jin G. J. Chem. Res. Synopses. 2002, 228.
  5. Zou, X. J.; Lai, L. H.; Jin, G.Y.; Zhang, Z. X. J. Agric. Food Chem. 2002, 50, 3757.
  6. Palaska, E.; Sohin, G; Kclicen, P.; Darlu, N. T.;Altinok, G. Farmaco 2002, 57, 101.
  7. Tyagi, M.; Kumar, A. Oriental. J. Chem. 2002, 18, 125.
  8. Clapp, L. B.; Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Ed.; Pergamon Press: Oxford, U. K., 1984; Vol. 6, p 365
  9. Afiatpour, A.; Srivastava, R. M.; Oliveira, M. L.;Barreiro, E. J. Braz. J. Med. Biol. Res. 1994, 27, 1403.
  10. Collins, T. J. In Green Chemistry Encyclopedia of Chemistry; Macmillan: New York, 1997
  11. Anastas, P. T.; Warner, J. C. Green Chemistry:Theory and Practice ; Oxford University Press:Oxford, U. K., 1998.
  12. Tundo, P.; Selva, M.;Marques, C. A.; Anastas, P. T.; Williamson, T. C. Green Chemistry: Designing Chemistry for the Environment ; Ed.; ACS Sym.: Washington DC, U. S. A., 1996; Vol. 81, p 626.
  13. Anastas, P. T.;Farris, C. T. Benign by Design: Alternative Synthetic Design for Pollution Prevention ; Ed.;ACS Sym.: Washington DC, U. S. A., 1994; p 557.
  14. Wilkinson, S. L. Chem. Eng. News. 1997, 75, 35.
  15. Anastas, P. T. Critical Rev. Anal. Chem. 1999, 29, 167.
  16. Tundo, P.; Anastas, P. T. Green Chemistry: Challenging Perspectives; Ed.; Oxford University Press: Oxford, U. K., 2000.
  17. Yadav, K. L.; Kumar, A.; Kumar S.; Singh, R. K. P. Transactions of the SAEST 2005, 40, 106.
  18. Kumar, A.; Kumar, S.; Singh, R. K. P. Proc. Nat. Acad. Sci. India, 2005, 75A IV, 233.
  19. Kumar, S.;Singh, R. K. P. J. Indian Chem. Soc. 2005, 82, 934.
  20. Kumar, S.; Yadav, P.; Singh, R. K. P. Transactions of the SAEST 2006, 41, 05.
  21. Yadav, K. L.; Kumar, S.; Kumar, A.; Singh, R. K. P. J. Indian Chem. Soc. 2004, 81, 595.
  22. Sharma, L. K.; Kumar, S.; Yadav, P.; Singh, R. K. P. Indian J Chem., Sec. B 2008, 47, 1277.
  23. Kumar, S.;Sharma, L. K.; Singh, R. K. P. J. Indian Chem. Soc. 2006, 83, 1160.
  24. Sharma, L. K.; Kumar, S.;Singh, R. K. P. Transactions of the SAEST 2006, 41, 48.
  25. Yadav, K. L.; Kumar, A.; Kumar, S.; Singh, R K P J Electrochem. Soc. 2003, 52(3), 114.
  26. Hetzheim, A.; Moeckel, K. Adv. Heterocyclic Chem. 1966; Vol. 7, p 183.
  27. Hill, J. In Comprehensive Heterocyclic Chemistry; Potts, K.T.,Ed.; Pergamon Press: Oxford, U. K., 1984; Vol. 6, p 427.
  28. Gani, R. S.; Pujar, S. S.; Gadaginamath, G. S. Indian J. Heterocycl. Chem., 2002, 12, 25.
  29. Golovlyova, S. M.; Moskvichey, Y. A.; Alov, E.M.; Kobylinsley, D. B.; Ermolaeva, V. V. Chem. Heterocycl. Compd. 2001, 37, 1102.
  30. Aboulwafa, O. M.; Omar, A. M. Sulfur Lett. 1992, 14, 181.
  31. Faidallah, H. M.; Sharshira, E. M.; Basaif, S. A.;A-Ba-Oum, A. E. Phos. Sulf. Sil. Rel. Elem. 2002, 67, 177.
  32. Cappo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Tetrahedron Lett. 2004, 45, 3257.

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