Advertisement

Addition–cyclization reactions of furan-2-carbonyl isothiocyanate with nitrogen nucleophiles as a synthetic route to novel azines and azoles of potential biological activity

  • Atef M. Abdel HamidEmail author
Original Paper
  • 19 Downloads

Abstract

Heterocyclization of furan-2-carbonyl isothiocyanate 1 with a variety of aliphatic and aromatic nitrogen nucleophiles resulted in the formation of a new series of heterocycles including triazines, pyrimidines, oxadiazines, imidazolidines, thiadiazoles and their condensed candidates. The antibacterial screening for a group of the newly synthesized compounds showed that they possess moderate antibacterial activities against examples of Gram-positive and Gram-negative bacteria.

Keywords

Anomeric-based oxidation Oxadiazine Quinazoline Thiadiazole Triazine 

References

  1. 1.
    Z. Arzehgar, S. Sajjadifar, H. Arandiyan, Asian J. Green Chem. 3, 43 (2019)Google Scholar
  2. 2.
    A. Ramazani, M. Khoobi, A. Torkaman, F.Z. Nasrabadi, H. Forootanfar, M. Shakibaie, M. Jafari, A. Ameri, S. Emami, M.A. Faramarzi, A. Foroumadi, A. Shafiee, Eur. J. Med. Chem. 78, 151 (2014)CrossRefGoogle Scholar
  3. 3.
    H. Aghahosseini, A. Ramazani, N.S. Jalayer, Z. Ranjdoost, A. Souldozi, K. Slepokura, T. Lis, Org. Lett. 21, 22 (2019)CrossRefGoogle Scholar
  4. 4.
    H. Parham, B.A. Esfahani, J. Iran. Chem. Soc. 5, 457 (2008)Google Scholar
  5. 5.
    I.E. Tolpygin, E.N. Shepelenko, G.S. Borodkin, A.D. Dubonosov, V.A. Bren, V.I. Minkin, Chem. Heterocycl. Compd. 46, 546 (2010)CrossRefGoogle Scholar
  6. 6.
    F. Aydin, N. Tunoglu, D. Aykac, Asian J. Chem. 25, 2455 (2013)CrossRefGoogle Scholar
  7. 7.
    M.M. Hemdan, A.F. Fahmy, N.F. Ali, E. Hegazi, A. Abd-Elhaleem, Chin. J. Chem. 25, 388 (2007)Google Scholar
  8. 8.
    M.G. Assy, H.Y. Moustafa, Phosphorous Sulfur Silicon Relat. Elem. 105, 213 (1995)CrossRefGoogle Scholar
  9. 9.
    E.V. Sadchikova, V.A. Bakulev, J.O. Subbotina, D.L. Privalova, W. Dehaen, K.V. Hecke, K. Robeyns, L.V. Meervelt, Tetrahedron 69, 6992 (2013)CrossRefGoogle Scholar
  10. 10.
    F. Piscitelli, C. Ballatore, A.B. Smith III, Bioorg. Med. Chem. Lett. 20, 648 (2010)CrossRefGoogle Scholar
  11. 11.
    O.V. Shablykin, A.V. Golovchenko, V.S. Brovarets, B.S. Drach, Russ. J. Gen. Chem. 77, 935 (2007)Google Scholar
  12. 12.
    B.A. Trofimov, J. Heterocycl. Chem. 36, 1490 (1999)CrossRefGoogle Scholar
  13. 13.
    R.V. Chambhare, B.G. Khadse, A.S. Bobde, R.H. Bahekar, Eur. J. Med. Chem. 38, 89 (2003)CrossRefGoogle Scholar
  14. 14.
    M.M.H. Bhuiyan, K.M.M. Rahman, M.K. Hossain, M.A. Rahim, M.I. Hossain, Croat. Chem. Acta 78, 633 (2005)Google Scholar
  15. 15.
    M.A. Salem, M.I. Marzouk, N.F. Mahmoud, J. Serb. Chem. Soc. 79, 1059 (2014)CrossRefGoogle Scholar
  16. 16.
    M. Hossam, D.S. Lasheen, N.S.M. Ismail, A. Esmat, A.M. Mansour, A.N.B. Singab, K.A.M. Abouzid, Eur. J. Med. Chem. 144, 330 (2018)CrossRefGoogle Scholar
  17. 17.
    A.A. Abu-Hashem, M.M. Youssef, Molecules 16, 1956 (2011)CrossRefGoogle Scholar
  18. 18.
    M.S. Frasinyuk, S.V. Gorelov, S.P. Bondarenko, V.P. Khilya, Chem. Heterocycl. Compd. 45, 1269 (2009)Google Scholar
  19. 19.
    E. Abdelghani, S.A. Said, M.G. Assy, A.M. Abdel Hamid, Arab. J. Chem. 10, S2926 (2017)CrossRefGoogle Scholar
  20. 20.
    H.A. El-Sayed, A.M. Abdel Hamid, M.G. Assy, T.S. Farag, Synth. Commun. 48, 794 (2018)Google Scholar
  21. 21.
    A.M. Abdel Hamid, W. Shehta, J. Iran. Chem. Soc. 15, 2771 (2018)CrossRefGoogle Scholar
  22. 22.
    S. Noura, M. Ghorbani, M.A. Zolfigol, M. Narimani, M. Yarie, M. Oftadeh, J. Mol. Liq. 271, 778 (2018)CrossRefGoogle Scholar
  23. 23.
    F. Karimi, M.A. Zolfigol, M. Yarie, Mol. Catal. 463, 20 (2019)CrossRefGoogle Scholar
  24. 24.
    M. Yarie, Iran. J. Catal. 7, 85 (2017)Google Scholar
  25. 25.
    A.R. Katritzky, P.J. Steel, S.N. Denisenko, Tetrahedron 57, 3309 (2001)CrossRefGoogle Scholar
  26. 26.
    B. Bonev, J. Hooper, J. Parisot, J. Antimicrob. Chemoth. 61, 1301 (2008)CrossRefGoogle Scholar
  27. 27.
    M. Uher, D. Ilavsky, J. Foltin, K. Skvareninova, Collect. Czech. Chem. Commun. 46, 3128 (1981)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceZagazig UniversityZagazigEgypt

Personalised recommendations