Skip to main content
SpringerLink
Log in

Facile TICl4-catalyzed synthesis of novel 1,2,4-triazoles appended to thiazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of sydnone-derived 3-aryl-5-methyl-1,3,4-oxadiazol-2(3H)-ones with thiourea and α-bromoacetophenone derivatives in the presence of a catalytic amount of TiCl4 produces 2-aryl-4-(4-aryl-1,3-thiazol-2-yl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-ones. The title compounds were screened for their antibacterial and antifungal activity. The toxicity of the compounds was evaluated in terms of mutagenicity, tumorigenicity, and reproductive effects. The drug-relevant properties (ClogP, drug-likeness, and drug score) were calculated, and the structure–activity relationship was discussed.

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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. R. R. Kamble, P. R. Latthe, and B. V. Badami, Heteroatom Chem., 18, 50 (2007).

    Article  CAS  Google Scholar 

  2. M. V. George and C. S. Angadiyavar, J. Org. Chem., 36, 1589 (1971).

    Article  CAS  Google Scholar 

  3. R. R. Kamble and B. S. Sudha, J. Heterocycl. Chem., 43, 345 (2006).

    Article  CAS  Google Scholar 

  4. A. Varvaresou, A. Tsantili-Kakoulidou, T. Siatra-Papastasikoudi, and E. Tiligada, Arzneim. Forsch., 50, 48 (2000).

    CAS  Google Scholar 

  5. M. Gokce, B. Cakir, K. Earl, and M. Sahin, Arch. Pharm., 334, 279 (2001).

    Article  CAS  Google Scholar 

  6. O. Pintilie, L. Profire, V. Sunel, M. Popa, and A. Pui, Molecules, 12 , 103 (2007).

    Article  CAS  Google Scholar 

  7. M. Foroumadi, M. Mirzaei, and A. Shafiee, Pharmazie, 56 , 610 (2001).

    CAS  Google Scholar 

  8. M. G. Mamolo, V. Falagiani, D. Zampieri, L. Vio, and F. Banfi, Farmaco, 56, 587 (2001).

    Article  CAS  Google Scholar 

  9. K. Zamani, K. Faghihi, I. Tofighi, and M. R. Shariatzadeh, Turk. J. Chem., 28, 95 (2004).

    CAS  Google Scholar 

  10. F. Clerici, D. Pocar, M. Guido, A. Loche, V. Perlini, and M. Brufani, J. Med. Chem., 44, 931 (2001).

    Article  CAS  Google Scholar 

  11. T. Önkol, B. Çakir, M. F. Şahin, E. Yildirim, and K. Erol. Turk. J. Chem., 28, 461 (2004).

    Google Scholar 

  12. S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, W. Filipelli, G. Falcone, L. Giordano, and M. Vitelli, Bioorg. Med. Chem., 9, 2149 (2001).

    Article  CAS  Google Scholar 

  13. L. Labanauskas, V. Kalcas, E. Udrenaite, P. Gaidelis, A. Brukštus, and V. Daukšas, Pharmazie, 56, 617 (2001).

    CAS  Google Scholar 

  14. S. Oniga, A. E. Parvu, B. Tiperciuc, M. Palage, and O. Oniga, Farmacia, 59, 44 (2011).

    CAS  Google Scholar 

  15. S. G. Wadodkar, S. O. Jinturkar, and A. V. Kasture, Indian Drugs, 16, 119 (1979).

    CAS  Google Scholar 

  16. A. Tsuruoka, Y. Kaku, H. Kakinuma, I. Tsukada, M. Yanagisawa, K. Nara, and T. Naito, Chem. Pharm. Bull., 46, 623 (1998).

    Article  CAS  Google Scholar 

  17. H. G. Roscoe, D. A. Blickans, and D. Kupfer, US Pat. 3752893 (1971); Chem. Abstr., 79, 96966 (1973).

    Google Scholar 

  18. I. Kayagil and S. Demirayak, Phosphorus, Sulfur, Silicon, Relat. Elem., 184, 2197 (2009).

    Article  CAS  Google Scholar 

  19. W. Weuffen, T. Pyl, W. Gruebner, and W. D. Juelich, Pharmazie, 20, 629 (1965).

    CAS  Google Scholar 

  20. C. F. H. Allen and A. Bell, Org. Synth., 24, 12 (1944).

    CAS  Google Scholar 

  21. R. M. Herbst and J. A. Garrison, J. Org. Chem., 18, 872 (1953).

    Article  CAS  Google Scholar 

  22. G. D. Buckley and N. H. Ray, J. Chem. Soc., 1156 (1949).

  23. C. Ainsworth and R. G. Jones, J. Am. Chem. Soc., 77, 621 (1955).

    Article  CAS  Google Scholar 

  24. W. Otting and H. A. Staab, Liebigs Ann. Chem., 622, 23 (1959).

    Article  CAS  Google Scholar 

  25. G. W. Sawdey, J. Am. Chem. Soc., 79, 1955 (1957).

    Article  CAS  Google Scholar 

  26. H. C. Brown, H. J. Gisler, Jr., and M. T. Cheng, J. Org. Chem., 31, 781 (1966).

    Article  CAS  Google Scholar 

  27. Y. T. Reddy, P. N. Reddy, B. S. Kumar, P. Rajput, N. Sreenivasulu, and B. Rajitha, Phosphorus, Sulfur, Silicon, Relat. Elem., 182, 161 (2007).

    Article  CAS  Google Scholar 

  28. H. Valizadeh, H. Gholipur, R. Zarrebin, M. Amiri, and M. R. Sabzi, Phosphorus, Sulfur, Silicon, Relat. Elem., 183, 1552 (2008).

    Article  CAS  Google Scholar 

  29. D. Basavaiah and A. J. Rao, Synth. Commun., 32, 195 (2002).

    Article  CAS  Google Scholar 

  30. L. Cai, C. Brouwer, K. Sinclair, J. Cuevas, and V. W. Pike, Synthesis, 133 (2006).

  31. S. G. Mallur and B. V. Badami, Farmaco, 55, 65 (2000).

    Article  CAS  Google Scholar 

  32. C. A. Lipinski, Drug Discovery Today: Technologies, 1, 337, (2004).

    Article  CAS  Google Scholar 

  33. OSIRIS Property Explorer, http://www.organic-chemistry.org/prog/peo.

  34. S. Emami, A. Kebriaeezadeh, N. Ahangar, and R. Khorasani, Bioorg. Med. Chem. Lett., 21, 655 (2011).

    Article  CAS  Google Scholar 

  35. A. T. Sangamwar, U. D. Deshpande, S. S. Pekamwar, and S. M. Vadvalkar, Ind. J. Biotechnol., 6, 389 (2007).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. PG Department of Studies in Chemistry, Karnatak University, Dharwad, 580003, India

    T. Gireesh, R. R. Kamble, R. K. Hunnur, T. Taj & M. Y. Kariduraganavar

Authors
  1. T. Gireesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. R. Kamble
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. K. Hunnur
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. Taj
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Y. Kariduraganavar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. R. Kamble.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1069–1078, July, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gireesh, T., Kamble, R.R., Hunnur, R.K. et al. Facile TICl4-catalyzed synthesis of novel 1,2,4-triazoles appended to thiazoles. Chem Heterocycl Comp 47, 877–885 (2011). https://doi.org/10.1007/s10593-011-0849-2

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0849-2

Keywords

Search

Navigation