Skip to main content
Log in

Solvent-free Preparation of 5-Aryloxytetrazoles via [2+3] Cycloaddition of Cyanates and Sodium Azide Using Silica Supported Sulfuric Acid as an Effective Heterogeneous Catalyst

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A simple and efficient method is described for the preparation of 5-aryloxytetrazoles in excellent yields and high purity from aryl cyanates using silica sulfuric acid as catalyst. The rate of product formation was enhanced by introduction of electron-donating substituents. The 1H NMR spectral characteristics of the products are also discussed.

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. T. L. Gilchrist, Heterocyclic Chemistry, Longman, London (1992).

    Google Scholar 

  2. M. Nasrollahzadeh, Y. Bayat, D. Habibi, and S. Moshaee, Tetrahedron Lett. 50, 4435 (2009).

    Article  CAS  Google Scholar 

  3. M. Nasrollahzadeh, D. Habibi, Z. Shahkarami, and Y. Bayat, Tetrahedron 65, 10715 (2009).

    Article  CAS  Google Scholar 

  4. A. R. Modarresi-Alam and M. Nasrollahzadeh, Turk. J. Chem., 33, 267 (2009).

    CAS  Google Scholar 

  5. D. Habibi and M. Nasrollahzadeh, Synth. Commun., 40, 3159 (2010).

    Article  CAS  Google Scholar 

  6. D. Habibi, M. Nasrollahzadeh, and Y. Bayat, Synth. Commun, 41, 2135 (2011).

    Article  CAS  Google Scholar 

  7. D. Habibi, M. Nasrollahzadeh, A. R. Faraji, and Y. Bayat, Tetrahedron, 66, 3866 (2010).

    Article  CAS  Google Scholar 

  8. D. Habibi, M. Nasrollahzadeh, and T. A. Kamali, Green Chem., 13, 3499 (2011).

    Article  CAS  Google Scholar 

  9. D. Martinand and A. Weise, Chem. Ber., 99, 317 (1966).

    Article  Google Scholar 

  10. A. R. Katritzky and S. K. Singh, ARKIVOC, xiii, 68 (2003).

  11. R. Katritzky, B. V. Rogovoy, and K. V. Kovalenko, Org. Chem., 68, 4941 (2003).

    Article  CAS  Google Scholar 

  12. J. Wiss, C. Fleury and U. Onken, Org. Process Res. Dev., 10, 349 (2006).

    Article  CAS  Google Scholar 

  13. A. H. Dabbagh, and A. R. Modarresi-Alam, J. Chem. Res., 44 (2000).

  14. A. R. Modarresi-Alam, H. Keykha, F. Khamooshi, and H. A. Dabbagh, Tetrahedron, 60, 1525 (2004).

    Article  CAS  Google Scholar 

  15. A. R. Modarresi-Alam and F. Khamooshi, Synth. Commun., 34, 129 (2004).

    Article  CAS  Google Scholar 

  16. A. R. Modarresi-Alam, F. Khamooshi, M. Rostamizadeh, H. Keykha, M. Nasrollahzadeh, H. R. Bijanzadeh, and E. Kleinpeter, J. Mol. Struct., 841, 61 (2007).

    Article  CAS  Google Scholar 

  17. H. A. Dabbagh and W. J. Lwowski, J. Org. Chem., 65, 7284 (2000).

    Article  CAS  Google Scholar 

  18. H. A. Dabbagh, A. R. Modarresi-Alam, A. Tadjarodi, and A. Taeb, Tetrahedron, 58, 2621 (2002).

    Article  CAS  Google Scholar 

  19. O. Subba Rao and W. Lwowski, Tetrahedron Lett., 21, 727 (1980).

    Article  Google Scholar 

  20. A. Subbaraj, O. Subba Rao, and W. Lwowski, J. Org. Chem., 54, 3945 (1989).

    Article  CAS  Google Scholar 

  21. H. A. Dabbagh and R. Karimzadeh, Molecules, 7, 189 (2002).

    Article  CAS  Google Scholar 

  22. T. J. Batterham, NMR Spectra of Simple Heterocycles, Wiley, New York (1973), p. 226.

    Google Scholar 

  23. R. N. Butler and V. C. Garvin, J. Chem. Soc., Perkin Trans. 1, 390 (1981).

  24. R. N. Butler, T. M. McEvoy, F. L. Scott, and J. C. Tobin, Can. J. Chem., 55, 1564 (1977).

    Article  CAS  Google Scholar 

  25. R. N. Butler, Can. J. Chem., 51, 2315 (1973).

    Article  CAS  Google Scholar 

  26. O. Subba Rao and W. Lwowski, J. Heterocycl. Chem., 17, 187 (1980).

    Article  Google Scholar 

  27. A. R. Modarresi-Alam, M. Nasrollahzadeh, and F. Khamooshi, ARKIVOC, xvi, 238 (2007).

  28. M. A. Zolfigol, F. Shirini, P. Salehi, and M. Abedini, Curr. Org. Chem., 12, 183 (2008).

    Article  Google Scholar 

  29. P. Salehi, M. A. Zolfigol, F. Shirini, and M. Baghbanzadeh, Curr. Org. Chem., 10, 2171 (2006).

    Article  CAS  Google Scholar 

  30. M. A. Zolfigol, Tetrahedron, 57, 9509 (2001).

    Article  CAS  Google Scholar 

  31. H. Eshghi, M. Rafei, and M. H. Karimi, Synth. Commun., 31, 771 (2001).

    Article  CAS  Google Scholar 

  32. A. R. Hajipour, B. Kooshki, and A. E. Ruoho, Tetrahedron Lett., 46, 5503 (2005).

    Article  CAS  Google Scholar 

  33. H. Eshghi and A. Hassankhani, Synth. Commun., 36, 2211 (2006).

    Article  Google Scholar 

  34. H. Eshghi, M. Rafie, Z. Gordi, and M. Bohloli, J. Chem. Res., 763 (2003).

  35. A. R. Hajipour, A. Zarei, L. Khazdooz, S. A. Pourmousavi, B. F. Mirjalili, and A. E. Ruoho, Phosphorus, Sulfur Silicon Relat. Elem., 180, 2029 (2005).

    Article  CAS  Google Scholar 

  36. H. Eshghi and Z. Gordi, Phosphorus, Sulfur Silicon Relat. Elem., 180, 1553 (2005).

    Article  CAS  Google Scholar 

  37. M. Mirjalili, M. A. Zolfigol, and A. Bamoniri, Phosphorus, Sulfur Silicon Relat. Elem., 179, 19 (2004).

    Article  CAS  Google Scholar 

  38. H. Eshghi and P. Shafieyoon, J. Chin. Chem. Soc., 52, 155 (2005).

    CAS  Google Scholar 

  39. M. Mirjalili, M. Zolfigol, A. Bamoniri, M. Amrollahi, and A. Hazar, Phosphorus, Sulfur Silicon Relat. Elem., 179, 1397 (2004).

    Article  CAS  Google Scholar 

  40. H. Eshghi and P. Shafieyoon, J. Chem. Res., 802 (2004).

  41. A. R. Modarresi-Alam, Ph. D. Thesis, Isfahan University of Technology, Isfahan (2000).

  42. F. Khamooshi and B. H. K. Jhaleh, J. Chil. Chem. Soc., 58, 1691 (2013).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to F. Khamooshi.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1578-1582, October, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khamooshi, F., Haghighi, B., Jhaleh, K. et al. Solvent-free Preparation of 5-Aryloxytetrazoles via [2+3] Cycloaddition of Cyanates and Sodium Azide Using Silica Supported Sulfuric Acid as an Effective Heterogeneous Catalyst. Chem Heterocycl Comp 49, 1464–1468 (2014). https://doi.org/10.1007/s10593-014-1397-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1397-3

Keywords

Navigation