Skip to main content
Log in

Sodium hypochlorite-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from hydrazides and aldehydes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A simple and convenient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed. Structurally divergent symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles can be obtained in moderate to high yields via NaOCl-mediated oxidative cyclization of N-acylhydrazones, generated in situ from aliphatic and aromatic hydrazides and aldehydes.

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

Access this article

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

Instant access to the full article PDF.

Figure 1.

Similar content being viewed by others

References

  1. (a) Reddy, E. K.; Remya, C.; Mantosh, K.; Sajith, A. M.; Omkumar, R. V.; Sadasivan, C.; Anwar, S. Eur. J. Med. Chem.2017, 139, 367. (b) Sajith, A. M.; Abdul Khader, K. K.; Joshi, N.; Reddy, M. N.; Padusha, M. S. A.; Nagaswarupa, H. P.; Nibin Joy, M.; Bodke, Y. D.; Karuvalam, R. P.; Banerjee, R.; Muralidharan, A.; Rajendra, P. Eur. J. Med. Chem.2015, 89, 21. (c) Reddy, E. K.; Remya, C.; Sajith, A. M.; Dileep, K. V.; Sadasivan, C.; Anwar, S. RSC Adv.2016, 6, 77431. (d) Yale, H. L.; Losee, K. J. Med. Chem.1966, 9, 478. (e) Adelstein, G. W. J. Med. Chem.1973, 16, 309. (f) Saunders, J.; Cassidy, M.; Freedman, S. B.; Harley, E. A.; Iversen, L. L.; Kneen, C.; MacLeod, A. M.; Merchant, K. J.; Snow, R. J.; Baker, R. J. Med. Chem.1990, 33, 1128. (g) Orlek, B. S.; Blaney, F. E.; Brown, F.; Clark, M. S. G.; Hadley, M. S.; Hatcher, J.; Riley, G. J.; Rosenberg, H. E.; Wadsworth, H. J.; Wyman, P. J. Med. Chem.1991, 34, 2726. (h) Fray, M. J.; Cooper, K.; Parry, M. J.; Richardson, K.; Steele, J. J. Med. Chem.1995, 38, 3514. (i) Omar, F. A.; Mahfouz, N. M.; Rahman, M. A. Eur. J. Med. Chem.1996, 31, 819. (j) Savitha, B.; Sajith, A. M.; Reddy, E. K.; Ananda Kumar, C. S.; Ali Padusha, M. S. ChemistrySelect2016, 1, 4721. (k) Leung, D.; Du, W.; Hardouin, C.; Cheng, H.; Hwang, I.; Cravatt, B. F.; Boger, D. L. Bioorg. Med. Chem. Lett.2005, 15, 1423.

  2. Unangst, P. C.; Shrum, G. P.; Connor, D. T.; Dyer, R. D.; Schrier, D. J. J. Med. Chem.1992, 35, 3691.

    Article  CAS  Google Scholar 

  3. Macaev, F.; Rusu, G.; Pogrebnoi, S.; Gudima, A.; Stingaci, E.; Vlad, L.; Shvets, N.; Kandemirli, F.; Dimoglo, A.; Reynolds, R. Bioorg. Med. Chem.2005, 13, 4842.

    Article  CAS  Google Scholar 

  4. Jones, R. M.; Leonard, J. N.; Buzard, D. J.; Lehmann, J. Expert Opin. Ther. Pat.2009, 19, 1339.

    Article  CAS  Google Scholar 

  5. Husain, A.; Ajmal, M. Acta Pharm.2009, 59, 223.

    Article  CAS  Google Scholar 

  6. Menteşe, E.; Ülker, S.; Kahveci, B. Chem. Heterocycl. Compd.2015, 50, 1671. [Khim. Geterotsikl. Soedin.2014, 1820.]

  7. (a) Meshram, G. A.; Vala, V. A. Chem. Heterocycl. Compd.2015, 51, 44. [Khim. Geterotsikl. Soedin.2015, 51, 44.] (b) Misra, H. K. Arch. Pharm.1983, 316, 487. b El-Emam, A. A.; Al-Deeb, O. A.; Al-Omar, M.; Lehmann, J. Bioorg. Med. Chem.2004, 12, 5107.

  8. (a) Chen, H.; Li, Z.; Han, Y. J. Agric. Food Chem.2000, 48, 5312. (b) Zou, X.-J.; Lai, L.-H.; Jin, G.-Y.; Zhang, Z.-X. J. Agric. Food Chem.2002, 50, 3757.

  9. Summa, V.; Petrocchi, A.; Bonelli, F.; Crescenzi, B.; Donghi, M.; Ferrara, M.; Fiore, F.; Gardelli, C.; Gonzalez Paz, O.; Hazuda, D. J.; Jones, P.; Kinzel, O.; Laufer, R.; Monteagudo, E.; Muraglia, E.; Nizi, E.; Orvieto, F.; Pace, P.; Pescatore, G.; Scarpelli, R.; Stillmock, K.; Witmer, M. V.; Rowley, M. J. Med. Chem.2008, 51, 5843.

    Article  CAS  Google Scholar 

  10. (a) James, N. D.; Growcott, J. W. Drugs Future2009, 34, 624. (b) Valente, S.; Trisciuoglio, D.; De Luca, T.; Nebbioso, A.; Labella, D.; Lenoci, A.; Bigogno, C.; Dondio, G.; Miceli, M.; Brosch, G.; Del Bufalo, D.; Altucci, L.; Mai, A. J. Med. Chem.2014, 57, 6259.

  11. Schlecker, R.; Thieme, P. C. Tetrahedron1988, 44, 3289.

    Article  CAS  Google Scholar 

  12. Hutt, M. P.; Elslager, E. F.; Werbel, L. M. J. Heterocycl. Chem.1970, 7, 511.

    Article  CAS  Google Scholar 

  13. (a) Küçükgüzel, Ş. G.; Oruç, E. E.; Rollas, S.; Şahin, F.; Özbek, A. Eur. J. Med. Chem.2002, 37, 197. (b) Ali, M. A.; Shaharyar, M. Bioorg. Med. Chem. Lett.2007, 17, 3314. (c) Zampieri, D.; Mamolo, M. G.; Laurini, E.; Fermeglia, M.; Posocco, P.; Pricl, S.; Banfi, E.; Scialino, G.; Vio, L. Bioorg. Med. Chem.2009, 17, 4693.

  14. Girges, M. M. Arzneimittelforschung1994, 44, 490.

    CAS  PubMed  Google Scholar 

  15. (a) Ogata, M.; Atobe, H.; Kushida, H.; Yamamoto, K. J. Antibiot.1971, 24, 443. (b) Johns, B. A. WO Patent 2004101512.

  16. Piatnitski, E.; Kiselyov, A.; Doody, J.; Hadari, Y.; Ouyang, S.; Chen, X. WO Patent 2004052280.

  17. Fray, M. J.; Cooper, K.; Parry, M. J.; Richardson, K.; Steele, J. J. Med. Chem.1995, 38, 3514.

    Article  CAS  Google Scholar 

  18. (a) Shi, W.; Qian, X.; Zhang, R.; Song, G. J. Agric. Food Chem.2001, 49, 124. (b) Zou, X.-J.; Lai, L.-H.; Jin, G.-Y.; Zhang, Z.-X. J. Agric. Food Chem.2002, 50, 3757. (c) Milinkevich, K. A.; Yoo, C. L.; Sparks, T. C.; Lorsbach, B. A.; Kurth, M. J. Bioorg. Med. Chem. Lett.2009, 19, 5796.

  19. (a) Martin, P. J.; Bruce, D. W. Liq. Cryst.2007, 34, 767. (b) Zhang, K.; Tao, Y.; Yang, C.; You, H.; Zou, Y.; Qin, J.; Ma, D. Chem. Mater.2008, 20, 7324. (c) Zhang, Y.; Zuniga, C.; Kim, S.-J.; Cai, D.; Barlow, S.; Salman, S.; Coropceanu, V.; Brédas, J.-L.; Kippelen, B.; Marder, S. Chem. Mater.2011, 23, 4002. (d) Simurova, N. V.; Maiboroda, O. I. Chem. Heterocycl. Compd.2019, 55, 604. [Khim. Geterotsikl. Soedin.2019, 55, 604.]

  20. (a) Wang, C.; Pålsson, L.-O.; Batsanov, A. S.; Bryce, M. R. J. Am. Chem. Soc.2006, 128, 3789. (b) Wu, C.-W.; Tsai, C.-M.; Lin, H.-C. Macromolecules2006, 39, 4298. (c) Li, A.-F.; Ruan, Y.-B.; Jiang, Q.-Q.; He, W.-B.; Jiang, Y.-B. Chem.– Eur. J.2010, 16, 5794.

  21. Stabile, P.; Lamonica, A.; Ribecai, A.; Castoldi, D.; Guercio, G.; Curcuruto, O. Tetrahedron Lett.2010, 51, 4801.

    Article  CAS  Google Scholar 

  22. (a) Padmavathi, V.; Reddy, G. S.; Padmaja, A.; Kondaiah, P.; Ali-Shazia Eur. J. Med. Chem.2009, 44, 2106. (b) Hamad, A.-S. S.; Hashem, A. I. J. Heterocycl Chem.2002, 39, 1325. (c) Kerr, V. N.; Ott, D. G.; Hayes, F. N. J. Am. Chem. Soc. 1960, 82, 186. (d) Da, Y.-X.; Yang, Z.; Quan, Z.-J.; Zhang, Z.; Wang, X.-C. J. Heterocycl. Chem.2009, 46, 737. (e) Rebek, J.; Gu, S.; Biros, S. US Patent 20060205728. (f) Borg, S.; Vollinga, R. C.; Labarre, M.; Payza, K.; Terenius, L.; Luthman, K. J. Med. Chem.1999, 42, 4331. (g) Rostamizadeh, S.; Ghamkhar, S. Chin. Chem. Lett.2008, 19, 639.

  23. Augustine, J. K.; Vairaperumal, V.; Narasimhan, S.; Alagarsamy, P.; Radhakrishnan, A. Tetrahedron2009, 65, 9989.

    Article  CAS  Google Scholar 

  24. Pouliot, M.-F.; Angers, L.; Hamel, J.-D.; Paquin, J.-F. Org. Biomol. Chem.2012, 10, 988.

    Article  CAS  Google Scholar 

  25. (a) Barrow, J. C.; Harrison, S.; Mulhearn, J.; Sur, C.; Williams, D. L.; Wolkenberg, S. WO Patent 2009146343. (b) Isobe, T.; Ishikawa, T. J. Org. Chem.1999, 64, 6989.

  26. (a) Shchekotikhin, A. E.; Shevtsova, E. K.; Traven’, V. F. Russ. J. Org. Chem.2007, 43, 1686. [Zh. Org. Khim.2007, 43, 1687.] (b) Johns, B. A.; Weatherhead, J. G.; Allen, S. H.; Thompson, J. B.; Garvey, E. P.; Foster, S. A.; Jeffrey, J. L.; Miller, W. H. Bioorg. Med. Chem. Lett.2009, 19, 1807. b Rajapakse, H. A.; Zhu, H.; Young, M. B.; Mott, B. T. Tetrahedron Lett.2006, 47, 4827.

  27. (a) Bethel, P. A.; Gerhardt, S.; Jones, E. V.; Kenny, P. W.; Karoutchi, G. I.; Morley, A. D.; Oldham, K.; Rankine, N.; Augustin, M.; Krapp, S.; Simader, H.; Steinbacher, S. Bioorg. Med. Chem. Lett.2009, 19, 4622. (b) Aquino, C. J.; Dickson, H.; Peat, A. J. WO Patent 2008157330. (c) Lee, S. H.; Seo, H. J.; Kim, M. J.; Kang, S. Y.; Song, K.-S.; Lee, S.-H.; Jung, M. E.; Kim, J.; Lee, J. Bioorg. Med. Chem. Lett.2009, 19, 1899.

  28. Guin, S.; Ghosh, T.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org. Lett.2011, 13, 5976.

    Article  CAS  Google Scholar 

  29. Gao, P.; Wei, Y. J. Chem. Res.2013, 37, 506.

    Article  CAS  Google Scholar 

  30. Gao, P.; Wei, Y. Heterocycl. Commun.2013, 19, 113.

    Article  CAS  Google Scholar 

  31. (a) Yu, W.; Huang, G.; Zhang, Y.; Liu, H.; Dong, L.; Yu, X.; Li, Y.; Chang, J. J. Org. Chem.2013, 78, 10337. (b) Majji, G.; Rout, S. K.; Guin, S.; Gogoi, A.; Patel, B. K. RSC Adv.2014, 4, 5357.

  32. Dobrotă, C.; Paraschivescu, C. C.; Dumitru, I.; Matache, M.; Baciu, I.; Ruţă, L. L. Tetrahedron Lett.2009, 50, 1886.

    Article  Google Scholar 

  33. Shang, Z.; Chu, Q.; Tan, S. Synthesis2015, 1032.

  34. Zhang, G.; Yu, Y.; Zhao, Y.; Xie, X.; Ding, C. Synlett2017, 1373.

  35. Kidwai, M.; Bhatnagar, D.; Mishra, N. K. Green Chem. Lett. Rev.2010, 3, 55.

    Article  CAS  Google Scholar 

  36. Singh, S.; Sharma, L. K.; Saraswat, A.; Srivastava, M. K.; Siddiqui, I. R.; Singh, R. K. P. Chem. Heterocycl. Compd.2014, 49, 1508. [Khim. Geterotsikl. Soedin.2013, 1626.]

  37. (a) Jasiak, K.; Kudelko, A.; Zieliński, W.; Kuźnik, N. ARKIVOC2017, (ii), 87. (b) Jasiak, K.; Kudelko, A. Tetrahedron Lett.2015, 56, 5878.

  38. Pore, D. M.; Mahadik, S. M.; Desai, U. V. Synth. Commun.2008, 38, 3121.

    Article  CAS  Google Scholar 

  39. (a) Okada, T.; Asawa, T.; Sugiyama, Y.; Kirihara, M.; Iwai, T.; Kimura, Y. Synlett2014, 596. (b) Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc.2006, 128, 8412. (c) Mirafzal, G. A.; Lozeva, A. M. Tetrahedron Lett.1998, 39, 7263.

  40. Polyak, F. D.; Eremeev, A. V.; Gavars, M. P.; Gaukhman, A. P.; Mazheika, I. B. Chem. Heterocycl. Compd.1988, 24, 733. [Khim. Geterotsikl. Soedin.1988, 894.]

  41. Ruan, L.; Shi, M.; Li, N.; Ding, X.; Yang, F.; Tang, J. Org. Lett.2014, 16, 733.

    Article  CAS  Google Scholar 

  42. Chen, C.-Y.; Andreani, T.; Li, H. Org. Lett.2011, 13, 6300.

    Article  CAS  Google Scholar 

  43. Yavolovsky, A. A.; Ivanov, E. I.; Ivanova, R. Yu. Chem. Heterocycl. Compd.2000, 36, 1359. [Khim. Geterotsikl. Soedin.2000, 1571.]

Download references

The authors thank University of Hyderabad for NMR spectroscopic analyses. Karuna Raman Paidi, Murali Krishna Kolli, and Venkata Ramana Pedakotla acknowledge Department of chemistry, Sri Krishnadevaraya University for laboratory facilities.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Venkata Ramana Pedakotla.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 371–376

Electronic supplementary material

ESM 1

(PDF 3369 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Paidi, K.R., Kolli, M.K., Reddy, E.K. et al. Sodium hypochlorite-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from hydrazides and aldehydes. Chem Heterocycl Comp 56, 371–376 (2020). https://doi.org/10.1007/s10593-020-02669-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02669-6

Keywords

Navigation