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.
Similar content being viewed by others
References
T. L. Gilchrist, Heterocyclic Chemistry, Longman, London (1992).
M. Nasrollahzadeh, Y. Bayat, D. Habibi, and S. Moshaee, Tetrahedron Lett. 50, 4435 (2009).
M. Nasrollahzadeh, D. Habibi, Z. Shahkarami, and Y. Bayat, Tetrahedron 65, 10715 (2009).
A. R. Modarresi-Alam and M. Nasrollahzadeh, Turk. J. Chem., 33, 267 (2009).
D. Habibi and M. Nasrollahzadeh, Synth. Commun., 40, 3159 (2010).
D. Habibi, M. Nasrollahzadeh, and Y. Bayat, Synth. Commun, 41, 2135 (2011).
D. Habibi, M. Nasrollahzadeh, A. R. Faraji, and Y. Bayat, Tetrahedron, 66, 3866 (2010).
D. Habibi, M. Nasrollahzadeh, and T. A. Kamali, Green Chem., 13, 3499 (2011).
D. Martinand and A. Weise, Chem. Ber., 99, 317 (1966).
A. R. Katritzky and S. K. Singh, ARKIVOC, xiii, 68 (2003).
R. Katritzky, B. V. Rogovoy, and K. V. Kovalenko, Org. Chem., 68, 4941 (2003).
J. Wiss, C. Fleury and U. Onken, Org. Process Res. Dev., 10, 349 (2006).
A. H. Dabbagh, and A. R. Modarresi-Alam, J. Chem. Res., 44 (2000).
A. R. Modarresi-Alam, H. Keykha, F. Khamooshi, and H. A. Dabbagh, Tetrahedron, 60, 1525 (2004).
A. R. Modarresi-Alam and F. Khamooshi, Synth. Commun., 34, 129 (2004).
A. R. Modarresi-Alam, F. Khamooshi, M. Rostamizadeh, H. Keykha, M. Nasrollahzadeh, H. R. Bijanzadeh, and E. Kleinpeter, J. Mol. Struct., 841, 61 (2007).
H. A. Dabbagh and W. J. Lwowski, J. Org. Chem., 65, 7284 (2000).
H. A. Dabbagh, A. R. Modarresi-Alam, A. Tadjarodi, and A. Taeb, Tetrahedron, 58, 2621 (2002).
O. Subba Rao and W. Lwowski, Tetrahedron Lett., 21, 727 (1980).
A. Subbaraj, O. Subba Rao, and W. Lwowski, J. Org. Chem., 54, 3945 (1989).
H. A. Dabbagh and R. Karimzadeh, Molecules, 7, 189 (2002).
T. J. Batterham, NMR Spectra of Simple Heterocycles, Wiley, New York (1973), p. 226.
R. N. Butler and V. C. Garvin, J. Chem. Soc., Perkin Trans. 1, 390 (1981).
R. N. Butler, T. M. McEvoy, F. L. Scott, and J. C. Tobin, Can. J. Chem., 55, 1564 (1977).
R. N. Butler, Can. J. Chem., 51, 2315 (1973).
O. Subba Rao and W. Lwowski, J. Heterocycl. Chem., 17, 187 (1980).
A. R. Modarresi-Alam, M. Nasrollahzadeh, and F. Khamooshi, ARKIVOC, xvi, 238 (2007).
M. A. Zolfigol, F. Shirini, P. Salehi, and M. Abedini, Curr. Org. Chem., 12, 183 (2008).
P. Salehi, M. A. Zolfigol, F. Shirini, and M. Baghbanzadeh, Curr. Org. Chem., 10, 2171 (2006).
M. A. Zolfigol, Tetrahedron, 57, 9509 (2001).
H. Eshghi, M. Rafei, and M. H. Karimi, Synth. Commun., 31, 771 (2001).
A. R. Hajipour, B. Kooshki, and A. E. Ruoho, Tetrahedron Lett., 46, 5503 (2005).
H. Eshghi and A. Hassankhani, Synth. Commun., 36, 2211 (2006).
H. Eshghi, M. Rafie, Z. Gordi, and M. Bohloli, J. Chem. Res., 763 (2003).
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).
H. Eshghi and Z. Gordi, Phosphorus, Sulfur Silicon Relat. Elem., 180, 1553 (2005).
M. Mirjalili, M. A. Zolfigol, and A. Bamoniri, Phosphorus, Sulfur Silicon Relat. Elem., 179, 19 (2004).
H. Eshghi and P. Shafieyoon, J. Chin. Chem. Soc., 52, 155 (2005).
M. Mirjalili, M. Zolfigol, A. Bamoniri, M. Amrollahi, and A. Hazar, Phosphorus, Sulfur Silicon Relat. Elem., 179, 1397 (2004).
H. Eshghi and P. Shafieyoon, J. Chem. Res., 802 (2004).
A. R. Modarresi-Alam, Ph. D. Thesis, Isfahan University of Technology, Isfahan (2000).
F. Khamooshi and B. H. K. Jhaleh, J. Chil. Chem. Soc., 58, 1691 (2013).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1578-1582, October, 2013.
Rights 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
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1397-3