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

Russian Journal of Organic Chemistry volume 55, pages 1961–1966 (2019)Cite this article

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.

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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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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

    CAS  Article  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 

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Authors and Affiliations

  1. Department of Applied Chemistry, College of Applied Sciences, University of Fallujah, Anbar, Iraq

    A. N. Ayyash

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  1. A. N. Ayyash
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Correspondence to A. N. Ayyash.

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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

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

Keywords

  • azetidin-2-ones
  • antimicrobial activity
  • pyromellitic diimide
  • pyridine-2-carbaldehyde
  • [2+2]-cyclo-addition