Synthesis of 1-benzyl-4-phenyl-1H-1,2,3-triazole via Click Reaction Using [Cu(CH3CN)4]PF6 as Catalyst
Main Article Content
Abstract
In this paper, [Cu(CH3CN)4]PF6 was used as a catalyst for the synthesis of 1-benzyl-4-phenyl-1H-1,2,3-triazole from phenylacetylene and benzyl azide via click reaction. 1-Phenyl-2-(trimethylsilyl)acetylene was synthesized via Sonogashira reaction, then the protecting group trimethylsilyl (−Si(CH3)3) was removed to obtain phenylacetylene. The structure of the obtained products was approved by modern spectroscopic methods like HRMS, FTIR, NMR.
Keywords:
1,4-disubstituted 1,2,3-triazole, click reaction, 1,2,3-triazole.
References
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[17] S. Mandal, S. Mandal, K. Geetharani, Zinc‐catalysed hydroboration of terminal and internal alkynes, Chemistry An Asian Journal. 2019. https://doi.org/10.1002/asia.201900839.
[18] N.T. Nguyen, J. Hofkens, I.G. Scheblykin, M. Kruk, W. Dehaen, Click reaction synthesis and photophysical studies of dendritic metalloporphyrins, Eur. J. Org. Chem. 2014 1766-1777. https://doi.org/10.1002/ejoc.201301158.
[2] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, A Stepwise Huisgen Cycloaddition Process: Copper(I)‐Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes, Angew. Chem. Int. Ed. Engl. 41 (2002) 2596-2599. https://doi.org/10.1002/1521-3773(20020715) 41:14<2596::AID-NIE2596>3.0.CO;2-4
[3] E. Shafran, V. Bakulev, Y. A. Rozin, Y. M. Shafran, Condensed 1,2,3-triazoles (review), Chem. Heterocycl. Com. 44 (2008) 1040-1069. https://doi.org/10.1007/s10593-008-0155-9.
[4] C.P. Kierkegaard, R. Norrestam, Copper(I) tetraacetonitrile perchlorate, Acta Crystallogr. B. 31 (1975) 314–317. https://doi.org/10.1107/s056 7740875002634.
[5] J.R. Black, W. Levason, M. Webster, Tetrakis(acetonitrile-N)copper(I) Hexafluorophos phate(V) Acetonitrile Solvate, Acta Cryst. C. 51 (1995) 623-625. https://doi.org/ 10.1107/S010827 0194012527.
[6] F.D.C. da Silva, M.C.B. de Souza, I. I. Frugulhetti, H. C. Castro, L. d. O. Silmara, T. M. L. de Souza, D. Q. Rodrigues, A. M. Souza, P. A. Abreu, F. Passamani, Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates, Eur. J. Med. Chem. 44 (2009) 373-383. https://doi.org/10.1016/j. ejmech.2008.02.047.
[7] M.J. Giffin, H. Heaslet, A. Brik, Y.-C. Lin, G. Cauvi, C.-H. Wong, D.E. McRee, J. H. Elder, C.D. Stout, B.E. Torbett, A copper(I)-catalyzed 1,2,3-triazole azide-alkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant, J. Med. Chem. 51 (2008) 6263-6270. https://doi.org/10.1021/jm800149m.
[8] A. Brik, J. Alexandratos, Y. C. Lin, J. H. Elder, A. J. Olson, A. Wlodawer, D. S. Goodsell, C. H. Wong, 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors, ChemBioChem. 6 (2005) 1167-1169. https://doi. org/10.1002/cbic.200500101.
[9] L.B. Peterson, B.S. Blagg, Click chemistry to probe Hsp90: Synthesis and evaluation of a series of triazole-containing novobiocin analogues, Bioorg. Med. Chem. Lett. 20 (2010) 3957-3960. https://doi.org/10.1016/j.bmcl.2010.04.140.
[10] B.F. Abdel-Wahab, H. A. Mohamed, G.E. Awad, Synthesis and biological activity of some new 1,2,3-triazole hydrazone derivatives, European Chemical Bulletin. 4 (2015) 106-109. http://dx. doi.org/10.17628/ecb.2015.4.106-109.
[11] P.A. Worthington, Synthesis of 1,2,4‐triazole compounds related to the fungicides flutriafol and hexaconazole, Pest. Manag. Sci. 31 (1991) 457-498. https://doi.org/10.1002/ps.2780310405.
[12] R.A.d. Silva, E.D. Quintela, G.M. Mascarin, J.A. F. Barrigossi, L.M. Lião, Compatibility of conventional agrochemicals used in rice crops with the entomopathogenic fungus Metarhizium anisopliae, Sci. agric. 70 (2013) 152-160. https:// doi.org/10.1590/S0103-90162013000300003.
[13] M. Nahrwold, T. Bogner, S. Eissler, S. Verma, N. Sewald, “Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue, Org. Let. 12 (2010) 1064-1067. https://doi.org/10.1021/ol1000 473.
[14] J. Doiron, R. Richard, M.M. Touré, N. Picot, R. Richard, M. Čuperlović-Culf, G. A. Robichaud, M. Touaibia, Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors, Eur. J. Med. Chem. 46 (2011) 4010-4024. https://doi.org/10.1016/j.ejmech.2011.05.074.
[15] M.F. Duarte, F. Martins, M.T. Fernandez, G.J. Langley, P. Rodrigues, M. T. Barros, M. L. Costa, Mass spectrometric study of aliphatic α‐carbonyl azides, Rapid. Commun. Mass. Sp. 17 (2003) 957-962. https://doi.org/10.1002/rcm.1005.
[16] G.W. Kabalka, L. Wang, R.M. Pagni, Sonogashira coupling and cyclization reactions on alumina: a route to aryl alkynes, 2-substituted-benzo[b]furans and 2-substituted-indoles, Tetrahedron. 57 (2001) 8017-8028. https://doi.org/10.1016/S0040-4020(01)00774-8.
[17] S. Mandal, S. Mandal, K. Geetharani, Zinc‐catalysed hydroboration of terminal and internal alkynes, Chemistry An Asian Journal. 2019. https://doi.org/10.1002/asia.201900839.
[18] N.T. Nguyen, J. Hofkens, I.G. Scheblykin, M. Kruk, W. Dehaen, Click reaction synthesis and photophysical studies of dendritic metalloporphyrins, Eur. J. Org. Chem. 2014 1766-1777. https://doi.org/10.1002/ejoc.201301158.