ISOINDOLINOTRIAZOLE DERIVATIVES: SYNTHESIS BY THE AZIDE-ALKYNE CYCLOADDITION CLICK CHEMISTRY
DOI:
https://doi.org/10.24297/jac.v10i7.6797Keywords:
Isoindolinone, triazole, click chemistryAbstract
A novel series of isoindolinotriazole derivatives with different substituents in the triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 2-(meta- or para-ethynylphenyl)-4,6-dimethoxyisoindolin-1-ones and several azides. The synthesized triazoles were characterized by IR, 1H NMR, 13C NMR and mass spectral techniques.
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References
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[17] Najahi, E., Sudor, J., Nepveu, F., et al. 2011. Click chemistry as an efficient tool to access 6-amino-5-cyano-2(1H)-pyrimidinone dimers. Heterocycl. lett. 1 (2011), 9-16
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[2] Fajardo, V., Elango, V., Cassels, B. K., et al. 1982. Chilenine: an isoindolobenzazepine alkaloid. Tetrahedron Lett. 23 (1982), 39-42
[3] Ferland, J.-M., Demerson, C. A., and Humber L. G. 1985. Synthesis of derivatives of isoindole and of pyrazino[2,1-a]isoindole. Can. J. Chem. 63 (1985), 361-365
[4] Linden, M., Hadler, D., and Hofmann, S. 1997. Randomized, double-blind, placebo-controlled trial of the efficacy and tolerability of a new isoindoline derivative (DN-2327) in generalized anxiety. Hum. Psychopharmacol. 12 (1997), 445-452
[5] Takahashi, I., Kawakami, T., Hirano, E., et al. 1996. Novel phthalimidine synthesis. mannich condensation of o-phthalaldehyde with primary amines using 1,2,3-1H-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries. Synlett 4 (1996), 353-355
[6] De Clercq, E. 1995. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38 (1995), 2491-2517
[7] New, K., Brechbiel, M. W. 2009. Growing applications of ‘‘click chemistry’’ for bioconjugation in contemporary biomedical research. Cancer Biother. Radiopharm. 24 (2009), 289-302
[8] Tornoe, C. W., Sanderson, S. J., Mottram, J. C., et al. 2004. Combinatorial library of peptidotriazoles: identification of [1,2,3]-triazole inhibitors against a recombinant Leishmania Mexicana cysteine protease. J. Comb. Chem. 6 (2004), 312-324
[9] Genin, M. J., Allwine, D. A., Anderson, D. J., et al. 2000. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenza and Moraxella catarrhalis. J. Med. Chem. 43 (2000), 953-970
[10] Alvarez, R., Velazquez, S., San-Felix, A., et al. 1994. 1,2,3-Triazole-[2',5'-bis-o-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5"-(4"-amino-1",2"-oxathiole 2",2"-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity. J. Med. Chem. 37 (1994), 4185-4194
[11] Singh, Y., Spinelli, N., De Francq, E., et al. 2006. A novel heterobifunctional linker for facile access to bioconjugates, Org. Biomol. Chem. 4 (2006), 1413-1419
[12] Dedola, S., Nepogodiev, S. A., and Field, R. A. 2007. Recent applications of the Cu(I)-catalysed Huisgen azide–alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry. Org. Biomol. Chem. 5 (2007), 1006-1017.
[13] Bock, V. D., Hiemstra, H., and van-Maarseveen, J. H. 2006. CuI-catalyzed alkyne–azide ‘‘click’’ cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006 (2006), 51-68
[14] Kolb, H. C., Finn, M. G., and Sharpless, K. B. 2001. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40 (2001), 2004-2021
[15] Gallos, J. K., and Koumbis, A. E. 2003. 1,3-Dipolar cycloadditions in the synthesis of carbohydrate mimics. Part 1: nitrile oxides and nitronates. Curr. Org. Chem. 7 (2003), 397-426
[16] Najahi, E., Sudor, J., Chabchoub, F., et al. 2010. Synthesis of 6-amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity. Molecules 15 (2010), 8841-8855
[17] Najahi, E., Sudor, J., Nepveu, F., et al. 2011. Click chemistry as an efficient tool to access 6-amino-5-cyano-2(1H)-pyrimidinone dimers. Heterocycl. lett. 1 (2011), 9-16
[18] Yoo, I. D., Ryoo, I. J., Kim, Y. H., et al. 2009. Novel clitocybin derivatives, preparation method thereof and composition containing the extract of clitocybe aurantiaca Kctc 11143bp or the novel clitocybin derivatives for prevention of aging as an active ingredient. Korea Res. Inst. Patent WO 2009102083.
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Published
2014-10-24
How to Cite
Rakotoarivelo, N. V., Najahi, E., & Perio, P. (2014). ISOINDOLINOTRIAZOLE DERIVATIVES: SYNTHESIS BY THE AZIDE-ALKYNE CYCLOADDITION CLICK CHEMISTRY. JOURNAL OF ADVANCES IN CHEMISTRY, 10(7), 2937–2943. https://doi.org/10.24297/jac.v10i7.6797
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