Synthesis of 1,5-disubstituted 1,2,3-triazole via multi-component reaction
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Từ khóa:
multi-component reaction
1,5-disubstituted 1,2,3-triazole
substituted 1,2,3-triazole
Tóm tắt
1,5-Disubstituted 1,2,3-triazoles are synthesized viametal-free multi-component reaction from primary amine, ketones and 4-nitrophenyl azide. The structure of three target compounds including:1-(4-methoxybenzyl)-5-(4-methylphenyl)-1H-1,2,3-triazole (1), 1-(4-methoxybenzyl)-5-(4-nitrophenyl)-1H-1,2,3-triazole (2) and 1-(4-methoxybenzyl)-5-phenyl-1H-1,2,3-triazole (3) is elucidated and identified by infrared spectroscopy, nuclear magnetic resonance spectroscopic analysis and high resolution mass spectrum. The formation of heterocyclic aromatic 1,2,3-triazole ring is approved by the appearance of singlet peak at 7.71 ppm in 1H NMR corresponding with triazolyl proton.
In addition, antibacterial and antifungal activities of products are also tested with three Gram-positive bacteria (B. subtilis, S. aureus and L. fermentum), three Gram-negative bacteria (P. aeruginosa, E.coli, S. enterica), and Candida albicans fungus.
In addition, antibacterial and antifungal activities of products are also tested with three Gram-positive bacteria (B. subtilis, S. aureus and L. fermentum), three Gram-negative bacteria (P. aeruginosa, E.coli, S. enterica), and Candida albicans fungus.
Tài liệu tham khảo
-
[1] M. D’hooghe, S. Vandekerckhove, K. Mollet, K. Vervisch, S. Dekeukeleire, L. Lehoucq, C. Lategan, P. J. Smith, K. Chibale, N. De Kimpe, “Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity”, Beilstein J. Org. Chem., 7, 2011, 1745–1752.
[2] M. Aufort, J. Herscovici, P. Bouhours, N. Moreau, C. Girard, “Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives”, Bioorganic Med. Chem. Lett., 18(3),2008, 195-1198.
[3] A. J. Salmon, M. L. Williams, Q. K. Wu, J. Morizzi, D. Gregg, S. A. Charman, D. Vullo, C. T. Supuran, “Metallocene-based inhibitors of cancer-associated carbonic anhydrase enzymes IX and XII”, J. Med. Chem, 55(11), 2012, 5506-5517.
[4] M. Whiting, J. Muldoon, Y. C. Lin, S. M. Silverman, W. Lindstrom, A. J. Olson, H. C. Kolb, M. Finn, K. B. Sharpless, J. H. Elder, “Inhibitors of HIV-1 protease by using in situ click chemistry”, Angew. Chem. Int. Ed. Engl., 45, 2006, 1435-1439.
[5] N. G. Aher, V. S. Pore, N. N. Mishra, A. Kumar, P. K. Shukla, A. Sharma, M. K. Bhat, “Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues”, Bioorganic Med. Chem. Lett.,19(3), 2009, 759-763.
[6] 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.
[7] P. Schmieder, R. Kühne, J. Rademann, “Metal‐Free, Regioselective Triazole Ligations that Deliver Locked cis Peptide Mimetics”, Angew. Chem. Int. Ed. Engl., 48(27), 2009, 5042-5045.
[8] M. Empting, O. Avrutina, R. Meusinger, S. Fabritz, M. Reinwarth, M. Biesalski, S. Voigt, G. Buntkowsky, H. Kolmar, ““Triazole bridge”: disulfide‐bond replacement by ruthenium‐catalyzed formation of 1,5‐disubstituted 1,2,3‐triazoles”, Angew. Chem. Int. Ed. Engl., 50(22), 2011, 5207-5211.
[9] G. Bianchetti, P. Dalla Croce, D. Pocar, “Studies on the schiff bases - enamines equilibrium”, Tetrahedron Lett., 6,1965, 2043-2045.
[10] J. Thomas, S. Jana, J. John, S. Liekens and W. Dehaen, “A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones”, Chem. Commun., 52, 2016, 2885-2888.
[11] S. Janaa, S. Iramb, J. Thomas, S. Liekens and W. Dehaen, “Synthesis and anticancer activity evaluation of novel aza-artemisinin derivatives”, Bioorg. Med. Chem., 25, 2017, 3671-3676.
[12] S. Jana, S. Iram, J. Thomas, M. Q. Hayat, C. Pannecouque and W. Dehaen, “Application of the triazolization reaction to afford dihydroartemisinin derivatives with anti-HIV activity”, Molecules, 22, 2017, 303.
[13] G. S. -Dorta, S. Jana, L. Borkova, J. Thomas and W. Dehaen, “Straightforward synthesis of enantiomerically pure 1,2,3-triazoles derived from amino esters”, Org. Biomol. Chem., 16, 2018, 3168-3176.
[14] N. Faucher, Y. Ambroise, J.-C. Cintrat, E. Doris, F. Pillon, B. Rousseau (), “Highly Chemoselective Hydrogenolysis of Iodoarenes”, J. Org. Chem., 67, 2002, 932-934.
[15] A. Aryangat, The MCAT Chemistry Book, 2015, 169-170.
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Jun 30, 2020
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Vo Viet Dai, Do Thi Phuong Thu, Nguyen Tran Nguyen. “Synthesis of 1,5-Disubstituted 1,2,3-Triazole via Multi-Component Reaction”. Tạp Chí Khoa học Và Công nghệ - Đại học Đà Nẵng, vol 18, số p.h 6, Tháng Sáu 2020, tr 77-81, doi:10.31130/jst-ud2020-102E.
