Nano TiO2–H3BO3 as an efficient and recycable catalyst for the synthesis of 5-substituted-1H-tetrazoles
الموضوعات : Iranian Journal of CatalysisFatemeh Abrishami 1 , Maryam Ebrahimikia 2 , Fatemeh Rafiee 3
1 - Department of Chemistry and Chemical Engineering,
Malek-Ashtar University of Technology, Tehran, Iran.
2 - Faculty of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran.
3 - Department of Chemistry, Alzahra University, Vanak, Tehran, Iran.
الکلمات المفتاحية: Heterogeneous catalyst, 5-Substituted-1H-tetrazoles, [3+2] Cycloaddition, Titanium oxide&ndash, boric acid, Recyclable,
ملخص المقالة :
An efficient method for the synthesis of 5-substituted-1H-tetrazoles through the reaction of nitriles with sodium azide using titanium oxide–supported boric acid (TiO2-H3BO3) catalyst was reported. The reactions were carried out at 120 °C and provided the corresponding tetrazoles in good to excellent yields. This method displayed significant advantages such as stability of the catalyst, high product yield, simple methodology, and easy work up. Also, this catalyst can be reused several times without loss of its catalytic activity. The aromatic nitriles with electron-donating and electron-withdrawing groups could be accomplished. The structural characteristics of the catalyst were identified by FT-IR, powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX) and inductively coupled plasma (ICP) analyses.
[1] E. P. Ellis, G. B. West, Progress in Medicinal Chemistry, vol. 17, Biomedical Press, 1980, p. 151.
[2] A. Rajasekaran, P. P. Thampi, Eur. J. Med. Chem. 40 (2005) 1359–1364.
[3] X. Y. Sun, C. X. Wei, X. Q. Deng, Z. G. Sun, Z. S. Quan, Pharmacol. Rep. 62 (2010) 273-277.
[4] R. Romagnoli, P. G. Baraldi, M. K. Salvador, D. Preti, M. A. Tabrizi, A. Brancale, X. H. Fu, J. Li, S. Z. Zhang, E. Hamel, R. Bortolozzi, G. Basso, G. Viola, J. Med. Chem. 55 (2011) 475-488.
[5] G. Navarrete-Vázquez, A. Alaniz-Palacios, S. Hidalgo-Figueroa, C. González-Acevedo, G. Ávila-Villarreal, S. Estrada-Soto, S. P. Webster, J. L. Medina-Franco, F. López-Vallejo, J. Guerrero-Álvarez, H. Tlahuext, Bioorg. Med. Chem. Lett. 23 (2013) 3244-3247.
[6] S. Sharma, M. C. Sharma, D. V. Kohli, J. Optoelectron. Biomed. Mater. 1 (2010) 59-72.
[7] P. Camilleri, M. W. Kerr, T. W. Newton, J. R. Bowyer, J. Agric. Food Chem. 37 (1989) 196-200.
[8] R. J. Nachman, G. M. Coast, K. Kaczmarek, H. J. Williams, J. Zabrocki, Acta Biochim. Pol. 51 (2004) 121-127.
[9] J. Li, S. Y. Chen, S. Tao, H. Wang, J. J. Li, S. Swartz, C. Musial, A. A. Hernandez, N. Flynn, B. J. Murphy, B. Beehler, K. E. Dickinson, L. Giupponi, G. Grover, R. Seethala, P. Sleph, D. Slusarchyk, M. Yan, W. G. Humphreys, H. Zhang, W. R. Ewing, J. A. Robl, D. Gordonb, J. A. Tino, Bioorg. Med. Chem. Lett. 18 (2008) 1825-1829.
[10] L. L. Dai, H. Z. Zhang, S. Nagarajan, S. Rasheed, C. H. Zhou, Med. Chem. Commun. 6 (2015) 147-154.
[11] M. A. Malik, S. A. Al-Thabaiti, M. A. Malik, Int. J. Mol. Sci. 13 (2012) 10880-10898.
[12] U. Natarajan, I. Kaliappan, N. K. Singh, Pharma Chem. 2 (2010) 159-167.
[13] M. D. Mullican, R. J. Sorenson, D. T. Connor, D. O. Thueson, J. A. Kennedy, M. C. Conroy, J. Med. Chem. 34 (1991) 2186-2194.
[14] T. Narasaiaha, D. Subba Raoa, S. Rasheeda, G. Madhavaa, D. Srinivasulua, P. Brahma Naidub, C. Naga Rajua, Pharm. Lett. 4 (2012) 854-862.
[15] T. Jin, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 45 (2004) 9435–9437.
[16] A. Burger, Prog. Drug Res. 37 (1991) 287–371.
[17] A. Hantzsch, A. Vagt, Justus Liebigs Ann. Chem. 314 (1901) 339-369.
[18] S. J. Wittenberger, B. G. Donner, J. Org. Chem. 58 (1993) 4139-4141.
[19] J. V. Duncia, M. E. Pierce, J. B. Santella, J. Org. Chem. 56 (1991) 2395-2400.
[20] Z. P. Demko, K. B. Sharpless, J. Org. Chem. 66 (2001) 7945-7950.
[21] Z. P. Demko, K. B. Sharpless, Org. Lett. 4 (2002) 2525-2527.
[22] D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccoro, J. Org. Chem. 69 (2004) 2896-2898.
[23] T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 49 (2008) 2824-2827
[24] H. A. Dabbagh, A. Najafi Chermahini, A. Teimouri, Heteroatom Chem. 17 (2006) 416-419.
[25] M. Esmaeilpour, J. Javidi, F. Nowroozi Dodeji, M. Mokhtari Abarghou, J. Mol. Catal. A: Chem. 393 (2014) 18–29.
[26] F. Abrishami, M. Ebrahimikia, F. Rafiee, Iran. J. Catal. 6 (2016) 245-251.
[27] S. M. Agawane, J. M. Nagarkar, Catal. Sci. Technol. 2 (2012) 1324–1327.
[28] Y. S. Gyoung, J. G. Shim, Y. Yamamoto, Tetrahedron Lett. 41 (2000) 4193-4196.
[29] L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu, G. Yin, Chem. Commun. 46 (2010) 448-450.
[30] B. Sreedhar, A. Suresh Kumar, D. Yada, Tetrahedron Lett. 52 (2011) 3565-3569.
[31] J. Bonnamour, C. Bolm, Chem. Eur. J. 15 (2009) 4543-4545.
[32] J. Roh, T. V. Atramonova, K. Vavrova, G. I. Koldobskii, A. Hrabalek, Synthesis 13 (2009) 2175-2178.
[33] H. Sharghi, S. Ebrahimpour moghaddam, M. Mahdi Doroodmand, J. Organomet. Chem. 738 (2013) 41-48.
[34] V. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 76 (2011) 9090-9095.
[35] C. Carlucci, B. F. Scremin, T. Sibillano, C. Giannini, E. Filippo, P. Perulli, A. L. Capodilupo, G. A. Corrente, G. Ciccarella, Inorganics 2 (2014) 264-277.
[36] G. A. Mansoori, T. Rohani Bastami, A. Ahmadpour, Z. Eshaghi, Annual Review of Nano Research, World Scientific, Washington, 2008, Vol. 2, Chap. 2.
[37] M. Parveen, F. Ahmad, A. M. Malla, S. Azaz, New J. Chem. 39 (2015) 2028-2041.
[38] W. Zhang, B. Yang, J. Chen, Int. J. Photoenergy 2012 (2012) 528637.
[39] A. Ansón-Casaos, M. J. Sampaio, C. Jarauta-Córdoba, M. T. Martínez, C. G. Silva, J. L. Faria, A. M. T. Silva, Chem. Eng. J. 277 (2015) 11-20.
[40] R. Beranek, H. Kisch, Photochem. Photobiol. Sci. 7 (2008) 40-48.
[41] D. R. Patil, M. B. Deshmukh, D. S. Dalal, J. Iran Chem. Soc. 9 (2012) 799-803.
[42] G. Qi, W. Zhang, Y. Dai, Res. Chem. Intermed. 41 (2015) 1149-1155.
[43] M. L. Kantam, V. Balasubrahmanyam, K. B. Shiva Kumar, Synth. Commun. 36 (2006) 1809-814.
[44] M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50 (2009) 4435-4438.
[45] A. Teimouri, A. Najafi Chermahini, Polyhedron 30 (2011) 2606-2610.
[46] S. K. Prajapti, A. Nagarsenkar, B. N. Babu, Tetrahedron Lett. 55 (2014) 3507-3510.
[47] M. Hosseini-Sarvari, S. Najafvand-Derikvandi, C. R. Chim. 17 (2014) 1007-1012.
[48] B. Nammalwar, N. Prasad Muddala, R. Pitchimani, R. A. Bunce, Molecules 20 (2015) 22757–22766.
[49] E. Wagner, J. Org. Chem. 38 (1973) 2976-2981.
[50] J. He, B. Li, F. Chen, Z. Xu, G. Yin, J. Mol. Catal. A: Chem. 304 (2009) 135-138.
[51] G. Qi, Y. Dai, Chin. Chem. Lett. 21 (2010) 1029-1032.
