Skip to main content
Log in

An efficient catalyst-free approach for the synthesis of novel isoxazolo[5,4-b]pyridine derivatives via one-pot three-component reaction

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A catalyst-free, one-pot, three-component condensation procedure for the synthesis of novel isoxazolo[5,4-b]pyridine derivatives has been reported by condensation of isatins, 3-methylisoxazol-5-amine, and cyclic enolizable carbonyl compounds in ethylene glycol at 80 °C. The structures of the synthesized compounds have been confirmed by spectral and X-ray studies. Crystal packing of one compound has also been reported. Less reaction time, easy work-up, and high yields are the important features of the present protocol.

Graphical abstract

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.

Fig. 1

Similar content being viewed by others

References

  1. Domling A (2006) Chem Rev 17:106

    Google Scholar 

  2. Ali A, Correa AG, Alves D, Zukerman-Schpector J, Westermann B, Ferreira MAB, Paixao MW (2014) Chem Commun 50:11926

    Article  CAS  Google Scholar 

  3. Murugan R, Anbazhagan S, Narayanan SS (2009) Eur J Med Chem 44:3272

    Article  CAS  PubMed  Google Scholar 

  4. Maheswari SU, Balamurugan K, Perumal S, Yogeeswari P, Sriram D (2010) Bioorg Med Chem Lett 20:7278

    Article  CAS  PubMed  Google Scholar 

  5. Karthikeyan K, Sivakumar PM, Doble M, Perumal PT (2010) Eur J Med Chem 45:3446

    Article  CAS  PubMed  Google Scholar 

  6. Kia Y, Osman H, Kumar RS, Murugaiyah V, Basiri A, Perumal S, Wahab HA, Bing CS (2013) Bioorg Med Chem 21:1696

    Article  CAS  PubMed  Google Scholar 

  7. Arun Y, Bhaskar G, Balachandran C, Ignacimuthu S, Perumal PT (2013) Bioorg Med Chem Lett 23:1839

    Article  CAS  PubMed  Google Scholar 

  8. Chen XQ, Pradhan T, Wang F, Kim JS, Yoon J (2012) Chem Rev 112:1910

    Article  CAS  PubMed  Google Scholar 

  9. Berkovic G, Krongauz V, Weiss V (2000) Chem Rev 100:1741

    Article  CAS  PubMed  Google Scholar 

  10. Lee CK, Davis DA, White SR, Moore JS, Sottos NR, Braun PV (2010) J Am Chem Soc 132:16107

    Article  CAS  PubMed  Google Scholar 

  11. Ye N, Chen H, Wold EA, Shi PY, Zhou J (2016) ACS Infect Dis 2:382

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Pavlovska TL, Redkin RG, Lipson VV, Atamanuk DV (2016) Mol Divers 20:299

    Article  CAS  PubMed  Google Scholar 

  13. Yu B, Zheng YC, Shi XJ, Qi PP, Liu HM (2016) Anti Cancer Agents Med Chem 16:1315

    Article  CAS  Google Scholar 

  14. Yu B, Yu DQ, Liu HM (2015) Eur J Med Chem 97:673

    Article  CAS  PubMed  Google Scholar 

  15. Galliford CV, Scheidt KA (2007) Angew Chem Int Ed 46:8748

    Article  CAS  Google Scholar 

  16. Edmonson S, Danishefsky SJ, Sepp-Lorenzino L, Rosen N (1999) J Am Chem Soc 121:2147

    Article  Google Scholar 

  17. Zhao V, Yu V, Sun W, Liu L, Lu J, McEachern D, Shargary S, Bernard D, Li X, Zhao T, Zou P, Sun D, Wang S (2013) J Med Chem 56:5553

    Article  CAS  PubMed  Google Scholar 

  18. Gupta S, Khanna G, Khurana JM (2016) Environ Chem Lett 14:559

    Article  CAS  Google Scholar 

  19. Gupta S, Saluja P, Khurana JM (2016) Tetrahedron 72:3986

    Article  CAS  Google Scholar 

  20. Kumari S, Singh H, Khurana JM (2016) Tetrahedron Lett 57:3081

    Article  CAS  Google Scholar 

  21. Khanna G, Saluja P, Khurana JM (2016) Tetrahedron Lett 57:5852

    Article  CAS  Google Scholar 

  22. Kumari S, Rajeshwari M, Khurana JM (2016) Aust J Chem 69:1049

    Article  CAS  Google Scholar 

  23. Saroha M, Khanna G, Khurana JM (2017) ChemistrySelect 2:7263

    Article  CAS  Google Scholar 

  24. Sheldrick GM (2008) Acta Crystallogr 64:112

    Article  CAS  Google Scholar 

  25. Farrugia LJ (2009) WinGX version 1.80.05: an integrated system of windows programs for the solution, refinement, and analysis of single crystal X-ray diffraction data. Department of Chemistry, University of Glasgow

Download references

Acknowledgements

K. M. thanks Dyal Singh College, DU, for the grant of Teacher Fellowship and S. K. thanks CSIR, New Delhi, India for JRF and SRF. Authors acknowledge University of Delhi for providing Research Grant and DST purse grant.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jitender M. Khurana.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 9694 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Meena, K., Kumari, S., Khurana, J.M. et al. An efficient catalyst-free approach for the synthesis of novel isoxazolo[5,4-b]pyridine derivatives via one-pot three-component reaction. Monatsh Chem 149, 1841–1848 (2018). https://doi.org/10.1007/s00706-018-2205-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2205-z

Keywords

Navigation