SBA-15-supported-dithizone-copper(I): An efficient heterogeneous catalyst for synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Document Type: Articles

Authors

Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran.

Abstract

In this work, the SBA-15-supported dithizone-copper(I) [SBA-15-dtz–Cu(I)] complex as a new heterogeneous catalyst is prepared for the first time. The catalyst prepared is characterized by the FT-IR spectroscopy, SEM, and ICP techniques. This reusable heterogeneous catalyst can be used in the click reactions for the green and facile synthesis of 1,4-disubstituted 1,2,3-triazolesvia a one-pot three-component reaction of benzyl chloride derivatives, terminal alkynes, and sodium azide in the water at 60 °C. A synthetic technique offering numerous advantages including environmentally friendly, high-to-excellent reaction yields, operational simplicity, short reaction times, reusability of the catalyst, and lack of an organic solvent was developed.

Keywords


[1] A. J. Burke, C. S. Marques, Catalytic Arylation Methods, From the Academic Lab to Industrial Processes, 1st Ed., Wiley-VCH, Weinheim, 2014, pp. 460-474.
[2] A. Lauria, R. Delisi, F. Mingoia, A. Terenzi, A. Martorana, G. Barone, A. M. Almerico, Eur. J. Org. Chem. (2014) 3289-3306.
[3] R. Huisgen, Angew. Chem. Int. Ed. 2 (1963) 656-688.
[4] R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984, pp. 1-176.
[5] C. Mitali, S. G. Praveen, K. Arvind, S. Diganta, Tetrahedron. Lett. 59 (2018) 397-401.
[6] A. A. Abdul, G. Dhrubajyoti, K. C. Amrita. K. B. Alak, S. Diganta, Bioorg. Med. Chem. Lett. 27 (2017) 3698-3703.
[7] C. Mitali, A. A. Abdul, B. Ankur, S. Diganta, J. Chem. Sci. 129 (2017) 1211-1217.
[8] A. A. Abdul, K. Manashjyoti, C. Mitali, S. Diganta, Tetrahedron. Lett. 57 (2016) 5661-5665.
[9] V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 41 (2002) 2596-2599.
[10] C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 67 (2002) 3057-3064.
[11] Y. M. A. Yamada, S.M. Sarkar, Y. Uozumi, J. Am. Chem. Soc. 134 (2012) 9285-9290.
[12] J.-M. Collinson, J. D. E. T. Wilton-Ely, S. Diez-Gonzalez, Chem. Commun. 49 (2013) 11358-11360.
[13] X. Xiong, H. Chen, Z. Tang, Y. Jiang, RSC. Adv. 4 (2014) 9830-9837.
[14] J. R. White, G. J. Price, S. Schiffers, P. R. Raithby, P. K. Plucinski, C. G. Frost, Tetrahedron. Lett. 51 (2010) 3913-3917.
[15] V. D. Bock, H. Henk, H. Jan, M. van, Eur. J. Org. Chem. (2006) 51-68
[16] A. K. Feldman, B. Colasson, V. V. Fokin, Org. Lett. 6 (2004) 3897-3899.
[17] P. Kočalka, N. K. Andersen, F. Jensen, P. Nielsen, Chem. Bio. Chem. 8 (2007) 2106-2116.
[18] Y-B. Zhao, Z-Y. Yan, Y-M. Liang, Tetrahedron. Lett. 47 (2006) 1545-1549.
[19] C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 67 (2002) 3057-3064.
[20] W. S. Brotherton, H. A. Michaels, J. T. Simmons, R. J. Clark, N. S. Dalal, L. Zhu, Org. Lett. 11 (2009) 4954-4957.
[21] J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 39 (2010) 1302-1315.
[22] L. Zhu, V. M. Lynch, E. V. Anslyn, Tetrahedron. 60 (2004) 7267-7275.
[23] D. Wang, S. Chen, B. Chen, Tetrahedron. Lett. 55 (2014) 7026-7028.
[24] F. Zhao, Y. Liu, S. Yang, K. Xie, Y. Jiang, Org. Chem. Front. 4 (2017) 1112-1115.
[25] E. Taheri, Z. Mirjafary, H. Saeidian, J. Mol. Struc. 1157 (2018) 418-424.
[26] M. Chetia, P. S. Gehlot, A. Kumar, D. Sarma, Tetrahedron. Lett. 59 (2017) 397-401.
[27] M. Gholinejad, N. Jeddi, ACS Sustainable Chem. Eng. 2 (2014) 2658-2665.
[28] S. Mohammed, A. K. Padala, B. A. Dar, B. Singh, B. Sreedhar, R. A. Vishwakarma, S. Bharate, Tetrahedron 68 (2012) 8156-8162.
[29] B.S.P. Anil Kumar, K. Harsha Vardhan Reddy, K. Karnakar, G. Satish, Y.V.D. Nageswar, Tetrahedron. Lett. 56 (2015) 1968-1972.
[30] B. Lai, Z. Huang, Z. Jia, R. Bai, Y. Gu, Catal. Sci. Technol. 6 (2016) 1810-1820.
[31] A. Shaygan-Nia, S. Ran, D. Döhler, X. Noirfalise, A. Belfiore, W. H. Binder, Chem. Commun. 50 (2014) 15374-15377.
[32] H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. Int. Ed. 43 (2004) 1983-1986.
[33] M. Bakherad, A. Keivanloo, A. H. Amin, P. Ghamari Kargar, Iran. J. Catal. 8 (2018) 179-187.
[34] M. Bakherad, F. Rezaeimanesh, H. Nasr-Isfahani, ChemistrySelect 3 (2018) 2594-2598.
[35] M. Bakherad, S. Karami, A. Keivanloo, S. Sepehri, ChemistrySelect 3 (2018) 11042-11047.
[36] K. Reddi Mohan Naidu, B. Satheesh Krishna, M. Anil Kumar, P. Arulselvan, S. Ibrahim Khalivulla, O. Lasekan, Molecules 17 (2012) 7543-7555.
[37] M. Bakherad, R. Doosti, M. Mirzaee, K. Jadidi, Iran. J. Catal. 7 (2017) 27-35.
[38] M. Bakherad, R. Doosti, M. Mirzaee, K. Jadidi, A. H. Amin, O. Amiri, Res. Chem. Intermed. 43 (2017) 7347-7363.
[39] M. Bakherad, A. Keivanloo, E. Moradian, A. H. Amin, R. Doosti, M. Armaghan, J. Iran. Chem. Soc. 15 (2018) 2811-2819.
[40] B. S. P. Anil Kumar, K. Harsha Vardhan Reddy, B. Madhav, K. Ramesh, Y. V. D. Nageswar, Tetrahedron Lett. 53 (2012) 4595-4599.
[41] S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 6 (2011) 2696-2718.
[42] G. Chouhan, G. Wang, H. Alper, Chem. Commun. 7 (2007) 4809-4811.
[43] D. Wang, N. Li, M. Zhao, W. Shi, C. Ma, B. Chen, Green Chem. 12 (2010) 2120-2123.
[44] F. Alonso, Y. Moglie, G. Radivoy, M. Yus, Tetrahedron Lett. 50 (2009) 2358-2362.
[45] I. S.-S. Juan, O.-T. Adrian, A. R. Ignacio, Arkivoc ix (2011) 177-188.
[46] M. Rivara, M. K. Patel, L, Amori, V. Zuliani, Bioorg. Med. Chem. Lett. 22 (2012) 6401-6404.
[47] S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 6 (2011) 2696-2718.
[48] J. Albadi, M. Keshavarz, Synth. Commun. 43 (2013) 2019-2030.
[49] J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 39 (2010) 1302-1315.
[50] K. Ladomenou, V. Nikolaou, G. Charalambidis, A. G. Coutsolelos, Coordination. Chem. Rev. 306 (2016) 1-42.
[51] M. Rivara, M. K. Patel, L, Amori, V. Zuliani, Bioorg. Med. Chem. Lett. 22 (2012) 6401-6404.
[52] M. Lakshmi Kantam, V. Swarna Jaya, B. Sreedhar, M. Mohan Rao, B.M. Choudary, J. Mol. Catal. A: Chem. 256 (2006) 273-277.
[53] H. Kang, H. J. Lee, J. C. Park, H. Song, K. H. Park, Top. Catal. 53 (2010) 523-528.