Skip to main content
Log in

Synthesis and Antimicrobial Screening of Novel Azetidin-2-ones Derived from Pyromellitic Diimide via [2+2]-Cycloaddition Reaction

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A series of novel 2-azetidinone derivatives have been obtained starting from pyromellitic dianhydride. Pyromellitic dianhydride was converted to pyromellitic diimide using sodium cyanate, and the diimide was alkylated with ethyl chloroacetate. The resulting diester was treated with hydrazine hydrate to obtain dihydrazide which reacted with substituted pyridine-2-carbaldehydes to give the corresponding Schiff bases, and [2+2]-cycloaddition of the latter with chloroacetyl chloride in the presence of triethylamine afforded the target azetidin-2-one derivatives. The newly synthesized compounds showed high antimicrobial activities against some bacterial and fungal strains.

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.

Similar content being viewed by others

References

  1. Fleming, A., Br. J. Exp. Pathol., 1929, vol. 10, p. 226. PMCID: PMC2048009

    CAS  PubMed Central  Google Scholar 

  2. Knowles, J.R., Acc. Chem. Res., 1985, vol. 18, p. 97. https://doi.org/10.1021/ar00112a001

    Article  CAS  Google Scholar 

  3. Patel, N.B. and Patel, J.C., Arab. J. Chem., 2011, vol. 4, p. 403. https://doi.org/10.1016/j.arabjc.2010.07.005

    Article  CAS  Google Scholar 

  4. Gurupadayya, B.M., Gopal, M., Padmashaly, B., and Manohara, Y., Indian J. Pharm. Sci., 2008, vol. 70, p. 572. https://doi.org/10.4103/0250-474X.45393

    Article  CAS  Google Scholar 

  5. Ishwar, B.K., Mubeen, M., and Kalluraya, B., Indian J. Heterocycl. Chem., 2003, vol. 13, p. 183.

    Google Scholar 

  6. Gilani, S.J., Nagarajan, K., Dixit, P.S., Taleuzzaman, M., and Khan, S.A., Arab. J. Chem., 2016, vol. 9, p. 1523. https://doi.org/10.1016/j.arabjc.2012.04.004

    Article  Google Scholar 

  7. Mohan, J. and Kumar, A., Indian J. Heterocycl. Chem., 2003, vol. 12, p. 189.

    Google Scholar 

  8. Halve, A.K., Bhadauria, D., and Dubey, R., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 341. https://doi.org/10.1016/j.bmcl.2006.10.064

    Article  CAS  Google Scholar 

  9. Jin, X., Zheng, C.J., Song, M.X., Wu, Y., and Sun, L.P., Eur. J. Med. Chem., 2012, vol. 56, p. 203. https://doi.org/10.1016/j.emech.2012.08,026

    Article  CAS  Google Scholar 

  10. Kishore, B. and Brahmeshwari, G., Indian J. Chem., Sect. B, 2018, vol. 57, p. 1042.

    Google Scholar 

  11. Jaberi, H.R., Fattahi, H., Ahmannasrollahi, A., Yarandpour, M., and Sedaghatizadeh, S., Org. Chem. Res., 2019, vol. 5, p. 42. https://doi.org/10.22036/ORG.CHEM.2018.133516.1150

    Google Scholar 

  12. Marri, S., Kakkerla, R., and Krishna, M.P.S., Indian J. Chem., Sect. B, 2019, vol. 58, p. 381.

    Google Scholar 

  13. Nikpour, F., Kazemi, S., and Sheikh, D., Heterocycles, 2006, vol. 68, p. 1559. https://doi.org/10.3987/COM-06-10762

    Article  CAS  Google Scholar 

  14. Gupta, A. and Halve, A.K., Open Chem. J., 2015, vol. 2, p. 1. https://doi.org/10.2174/1874842201502010001

    Article  Google Scholar 

  15. Arthington-Skaggs, B., Motley, M., and Morrison, C.J., J. Clin. Microbiol., 2000, vol. 38, p. 2254.

    CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. N. Ayyash.

Additional information

Conflict of Interests

The author declares no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ayyash, A.N. Synthesis and Antimicrobial Screening of Novel Azetidin-2-ones Derived from Pyromellitic Diimide via [2+2]-Cycloaddition Reaction. Russ J Org Chem 55, 1961–1966 (2019). https://doi.org/10.1134/S1070428019120261

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019120261

Keywords

Navigation