Skip to main content
SpringerLink
Log in

Facile Synthesis of Isoniazid Derivatives – 1-[2-(3-Aryl(Hetaryl)-1-Phenyl-1H-Pyrazol-4-yl)-5-(Pyridin-4-yl)-1,3,4-Oxadiazol-3(2H)-yl]Ethanones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A facile and efficient ultrasound-aided approach has afforded cyclization of isoniazid hydrazones into 2,5-bishetaryloxadiazolines at ambient temperature. Acetic anhydride helped in intramolecular oxidative cyclization along with N-acylation of oxadiazoline. The synthesized 1-[2-(1-phenyl-1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl]ethanones were isolated in good yields, spectral data supported the proposed structures.

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. Cravotto, G.; Cintas, P. Chem. Soc. Rev.2006, 35, 180.

    Article  CAS  Google Scholar 

  2. Patil, R.; Bhoir, P.; Deshpande, P.; Wattamwar, T.; Shirude, M.; Chaskar, P. Ultrason. Sonochem.2013, 20, 1327.

    Article  CAS  Google Scholar 

  3. Banerjee, B. Ultrason. Sonochem.2017, 35, 15.

    Article  CAS  Google Scholar 

  4. (a)Fox, H. H. J. Org. Chem.1952, 17, 542. (b) Vilcheze, C.; Jacobs, W. R., Jr. Annu. Rev. Microbiol.2007, 61, 35.

  5. Lohrasbi, V.; Talebi, M.; Bialvaei, A. Z.; Fattorini, L.; Drancourt, M.; Heidary, M.; Darban-Sarokhalil, D. Tuberculosis2018, 109, 17.

    Article  CAS  Google Scholar 

  6. (a) Bora, R. O.; Dar, B.; Pradhan, V.; Farooqui, M. Mini-Rev. Med. Chem.2014, 14, 355. (b) Hu, Y.; Li, C.-Y.; Wang, X.-M.; Yang, Y.-H; Zhu, H- L. Chem. Rev.2014, 114, 5572.

  7. (a) Esvan, Y. J.; Giraud, F.; Pereira, E.; Suchaud, V.; Nauton, L.; Thery, V.; Dezhenkova, L. G.; Kaluzhny, D. N.; Mazov, V. N.; Shtil, A. A.; Anizon, F.; Moreau, P. Bioorg. Med. Chem.2016, 24, 3116. (b) Ali, I.; Lone, M. N.; Aboul-Enein, H. Y. MedChemComm2017, 8, 1742.

  8. Maliyappa, M. R.; Keshavayya, J.; Mahanthappa, M.; Shivaraj, Y.; Basavarajappa, K. V. J. Mol. Struct.2020, 1199, 126959.

    Article  CAS  Google Scholar 

  9. Sarojini, B. K.; Bello, K.; Holla, B. S.; Subrahmanya, M. M. Opt. Mater.2019, 89, 80.

    Article  Google Scholar 

  10. Yildiz, B.; Güzel, E.; Akyüz, D.; Arslan, B. S.; Koca, A.; Şener, M. K. Sol. Energy2019, 191, 654.

    Article  CAS  Google Scholar 

  11. Li, T.; Wen, G.; Li, J.; Zhang, W.; Wu, S. Molecules2019, 24, 1490.

    Article  Google Scholar 

  12. Mihailović, N.; Marković, V.; Matić, I. Z.; Stanisavljević, N. S.; Jovanović, Ž. S.; Trifunović, S.; Joksović, L. RSC Adv.2017, 7, 8550.

    Article  Google Scholar 

  13. Kudelko, A.; Zielinski, W. Tetrahedron Lett. 2012, 53, 76.

    Article  CAS  Google Scholar 

  14. Ramazani, A.; Ahmadi, Y.; Mahyari, A. Synth. Commun.2011, 41, 2273.

    Article  CAS  Google Scholar 

  15. Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Chem. Rev.2014, 114, 2942.

    Article  CAS  Google Scholar 

  16. Dobrotã, C.; Paraschivescu, C. C.; Dumitru, I.; Matache, M.; Baciu, I.; Rutã, L. L. Tetrahedron Lett. 2009, 50, 1886.

    Article  Google Scholar 

  17. Pardeshi, S. P.; Patil, S. P.; Bobade, V. D. Synth. Commun. 2010, 40, 1601.

    Article  CAS  Google Scholar 

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

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

    Article  CAS  Google Scholar 

  20. Chen, D. W.; Chen, Z. C. Synth. Commun. 1995, 25, 1617.

    Article  CAS  Google Scholar 

  21. Zheng, X.; Li, Z.; Wang, Y.; Chen, W.; Huang, Q.; Liu, C.; Song, G. J. Fluorine Chem. 2003, 123, 163.

    Article  CAS  Google Scholar 

  22. (a) Desai, N. C.; Somani, H.; Trivedi, A.; Bhatt, K.; Nawale, L.; Khedkar, V. M.; Jha, P. C.; Sarkar, D. Bioorg. Med. Chem. Lett.2016, 26, 1776. (b) Desai, N. C.; Kotadiya, G. M.; Trivedi, A. R.; Khedkar, V. M.; Jha, P. C. Med. Chem. Res. 2016, 25, 2698. (c) Desai, N. C.; Kotadiya, G. M. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.2014, 53B, 1159.

  23. Abdel-Wahab, B. F.; Khidre, R. E.; Farahat, A. A. ARKIVOC2011, (i), 196.

  24. (a) Vora, J. J.; Vasava, S. B.; Parmar, K. C.; Sharma, S. S.; Patel, J. A.; Brahmbhatt, M. P. Int. J. Chem. Sci.2009, 7, 405. (b) Nayak, N.; Ramprasad, J.; Dalimba, U. Bioorg. Med. Chem. Lett.2015, 25, 5540.

  25. Lee, L.; Robb, L. M.; Lee, M.; Davis, R.; Mackay, H.; Chavda, S.; Babu, B.; O'Brien, E. L.; Risinger, A. L.; Mooberry, S. L.; Lee, M. J. Med. Chem.2009, 53, 325.

    Article  Google Scholar 

  26. (a) Wang, L.-N.; Han, D.; Xu, F.-F.; Meng, X.-B.; Li, Z.-J. Carbohydr. Res.2009, 344, 2113. (b) Maccioni, E.; Alcaro, S.; Cirilli, R.; Vigo, S.; Cardia, M. C.; Sanna, M. L.; Meleddu, R.; Yanez, M.; Costa, G.; Casu, L.; Matyus, P.; Distinto, S. J. Med. Chem.2011, 54, 6394. (c) de Oliveira, C. S.; Lira, B. F.; Barbosa-Filho, J. M.; Lorenzo, J. G. F.; de Menezes, C. P.; dos Santos, J. M. C. G.; de O. Lima, E.; de Athayde-Filho, P. F. J. Braz. Chem. Soc.2013, 24, 115.

  27. Alhadi, A. A.; Othman, R.; Yehye, W. A.; Rahman, N. A. Tetrahedron Lett.2015, 56, 573.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Kinnaird College for Women Lahore, 93-Jail Road, Lahore, 54000, Pakistan

    Faryal Chaudhry

  2. Institute of Chemistry, University of the Punjab, Quaid-e-Azam Campus, Lahore, 54590, Pakistan

    Faryal Chaudhry, Munawar Ali Munawar & Misbahul Ain Khan

  3. Department of Chemistry, The Islamia University of Bahawalpur Pakistan, Bahawalpur, 63100, Pakistan

    Misbahul Ain Khan

Authors
  1. Faryal Chaudhry
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Munawar Ali Munawar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Misbahul Ain Khan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Faryal Chaudhry or Munawar Ali Munawar.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 615–618

Electronic supplementary material

ESM1

(PDF 4276 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chaudhry, F., Munawar, M.A. & Khan, M.A. Facile Synthesis of Isoniazid Derivatives – 1-[2-(3-Aryl(Hetaryl)-1-Phenyl-1H-Pyrazol-4-yl)-5-(Pyridin-4-yl)-1,3,4-Oxadiazol-3(2H)-yl]Ethanones. Chem Heterocycl Comp 56, 615–618 (2020). https://doi.org/10.1007/s10593-020-02708-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02708-2

Keywords

Search

Navigation