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Abstract
We report a novel methodology for the efficient and rapid synthesis of core intermediate 2-(2H-1,2,3-triazol-2-yl)benzoic acid using trans-N,N’-dimethylcyclohexane-1,2-diamine as a catalyst and copper iodide as co-catalyst under microwave irradiations and a series of novel N-phenyl-2-(2H-1,2,3-triazol-2-yl)benzamide derivatives via acid-amine coupling reaction using DCC as a dehydrating agent and DMAP as a base. In comparison to the conventional heating procedure and performing the reaction using different combinations of catalysts and bases, the time of synthesis and efforts are significantly reduced in the present method, which also gave excellent yield. The scaffold and all novel amides were characterized by spectroscopic techniques.
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References
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- F. de Carvalho da Silva, M.F. do Carmo Cardoso, P.G. Ferreira and V.F. Ferreira, eds.: W. Dehaen and V. Bakulev, Biological Properties of 1H-1,2,3- and 2H-1,2,3-Triazoles, In: Chemistry of 1,2,3-Triazoles, Topics in Heterocyclic Chemistry, Springer, Cham, vol. 40 (2014); https://doi.org/10.1007/7081_2014_124.
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References
P. Singh, R. Raj, V. Kumar, M.P. Mahajan, P.M.S. Bedi, T. Kaur and A.K. Saxena, 1,2,3-Triazole Tethered b-Lactam-Chalcone Bifunc-tional Hybrids: Synthesis and Anticancer Evaluation, Eur. J. Med. Chem., 47, 594 (2012); https://doi.org/10.1016/j.ejmech.2011.10.033.
B.F. Abdel-Wahab, E. Abdel-Latif, H.A. Mohamed and G.E.A. Awad, Design and Synthesis of New 4-Pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-Triazol-4-yl-pyrazolin-1-ylthiazoles as Potential Antimicrobial Agents, Eur. J. Med. Chem., 52, 263 (2012); https://doi.org/10.1016/j.ejmech.2012.03.023.
V.F. Ferreir, D.R. da Roch, F.C. da Silva, P.G. Ferreira, N.A. Boechat and J.L. Magalhães, Novel 1H-1,2,3-, 2H-1,2,3-, 1H-1,2,4- and 4H-1,2,4-triazole Derivatives: A Patent Review (2008 -2011), Expert Opin. Therap. Patents, 23, 319 (2013); https://doi.org/10.1517/13543776.2013.749862.
Q. Tian, X. Chen, W. Liu, Z. Wang, S. Shi and C. Kuang, Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp2 C-H Activation. Org. Biomol. Chem., 11, 7830 (2013); https://doi.org/10.1039/c3ob41558a.
F. de Carvalho da Silva, M.F. do Carmo Cardoso, P.G. Ferreira and V.F. Ferreira, eds.: W. Dehaen and V. Bakulev, Biological Properties of 1H-1,2,3- and 2H-1,2,3-Triazoles, In: Chemistry of 1,2,3-Triazoles, Topics in Heterocyclic Chemistry, Springer, Cham, vol. 40 (2014); https://doi.org/10.1007/7081_2014_124.
S. Haider, M.S. Alam and H. Hamid, 1,2,3-Triazoles: Scaffold with Medicinal Significance, Inflamm. Cell Signal., 1, e95 (2014).