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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 3
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Original Articles

Simple synthesis of 1-substituted-4-vinyl-1,2,3-triazoles based on polystyrene-supported sulfonyl chloride

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Pages 226-231 | Received 13 Aug 2015, Published online: 06 Feb 2016

References

  • Fan, W. Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R. Rees, C. W. Scriven, C. W. V. (Eds.); Elsevier: Oxford, 1996; Vol. 4, pp 1–126.
  • (a) Krasiski, A.; Radi, Z.; Manetsch, R.; Raushel, J.; Taylor, P.; Sharpless, K. B.; Kolb, H. C. In situ selection of lead compounds by click chemistry: Target-guided optimization of acetylcholinesterase inhibitors. J. Am. Chem. Soc. 2005, 127, 6686–6692; (b) Binder, W. H.; Kluger, C. Azide/alkyne-“click” reactions: Application in material science and organic synthesis. Curr. Org. Chem. 2006, 10, 1791–1815; (c) Suijkerbuijk, B. M. J. M.; Aerts, B. N. H.; Dijkstra, H. P.; Lutz, M.; Spek, A. L.; Koten, G. V.; Gebbink, R. J. M. K. “Click” 1,2,3-triazoles as tunable ligands for late transition metal complexes. Dalton Trans. 2007, 1273–1276; (d) Moorhouse, A. D.; Moses, J. E. Click chemistry and medicinal chemistry: A case of cyclo-addition. ChemMedChem. 2008, 3, 715–723; (e) Amblard, F.; Cho, J. H.; Schinazi, R. F. Cu(I)-catalyzed Huisgen azide−alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry. Chem. Rev. 2009, 109, 4207–4220; (f) Holub, J. M.; Kirshenbaum, K. Tricks with clicks: Modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition. Chem. Soc. Rev. 2010, 39, 1325–1337; (g) Agalave, S. G.; Maujan, S. R.; Pore, V. S. Click chemistry: 1,2,3-Triazoles as pharmacophores. Chem.–Asian. J. 2011, 6, 2696–2718 (h) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Click chemistry for drug development and diverse chemical–biology applications. Chem. Rev. 2013, 113, 4905–4979.
  • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem., Int. Ed. 2002, 41, 2596–2599.
  • Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper (I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057–3064.
  • For recent reviews, see (a) Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. CuI-catalyzed alkyne–azide “click” cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 51–68; (b) Gil, M. V.; Arevalo, M. G.; Lopez, O. Click chemistry: What’s in a name? Triazole synthesis and beyond. Synthesis 2007, 1589–1620; (c) Meldal, M.; Tornøe, C. W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 2008, 108, 2952–3015; (d) Kappe, C. O.; Van der Eycken, E. Click chemistry under non-classical reaction conditions. Chem. Soc. Rev. 2010, 39, 1280–1290; (e) Hein, J. E.; Fokin, V. V. Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: New reactivity of copper (I) acetylides. Chem. Soc. Rev. 2010, 39, 1302–1315.
  • Wouters, G.; Smets, G. Copolymerization of C-vinyltriazoles and C-vinyltetrazole with vinyl monomers. Makromol. Chem. 1982, 183, 1861–1868.
  • (a) Feldman, A. K.; Colasson, B.; Fokin, V. V. One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides. Org. Lett. 2004, 6, 3897–3899; (b) Thibault, R. J.; Takizawa, K.; Lowenhielm, P.; Helms, B.; Mynar, J. L.; Fréchet, J. M. J.; Hawker, C. J. A versatile new monomer family: Functionalized 4-vinyl-1,2,3-triazoles via click chemistry. J. Am. Chem. Soc. 2006, 128, 12084–12085; (c) Takizawa, K.; Nulwala, H.; Thibault, R. J.; Lowenhielm, P.; Yoshinaga, K.; Wooley, K. L.; Hawker, C. J. Facile syntheses of 4-vinyl-1,2,3-triazole monomers by click azide/acetylene coupling. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 2897–2912; (d) Nulwala, H.; Burke, D. J.; Khan, A.; Serrano, A.; Hawker, C. J. N-Vinyltriazoles: A new functional monomer family through click chemistry. Macromolecules 2010, 43, 5474–5477.
  • (a) Reddy, M. N.; Swamy, K. C. K. Facile construction of [6,6]-, [6,7]-, [6,8]-, and [6,9]-ring-fused triazole frameworks by copper-catalyzed, tandem, one-pot, click, and intramolecular arylation reactions: Elaboration to fused pentacyclic derivatives. Eur. J. Org. Chem. 2012, 2013–2022; (b) Brahma, K.; Achari, B.; Chinmay Chowdhury, C. Facile synthesis of [1,2,3]-triazole-fused isoindolines, tetrahydroisoquinolines, benzoazepines, and benzoazocines by palladium-copper catalysed heterocyclisation. Synthesis 2013, 545–555; (c) Carcenac, Y.; David-Quillot, F.; Abarbri, M.; Duchêne, A.; Thibonnet, J. Palladium-catalyzed cross-coupling of 1,4-disubstituted 5-iodo-1,2,3-triazoles with organotin reagents. Synthesis 2013, 633–638; (d) Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Alkenes as azido precursors for the one-pot synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon. J. Org. Chem. 2013, 78, 5031–5037.
  • Wang, Q.-Y.; Sheng, W.-S.; Sheng, S.-R.; Li, Y.; Cai, M.-Z. Click chemistry on polymer support: Synthesis of 1-vinyl- and 1-allyl-1,2,3-triazoles via selenium linker. Synth. Commun. 2014, 44, 59–67.
  • Young, D. D.; Deiters, A. Solid-Phase Organic Synthesis: Concepts, Strategies, and Applications; Toy, P. H. Lam, Y. (Eds.); John Wiley & Sons, Inc.: Hoboken, NJ, 2012; pp. 171–201.
  • ten Holte, P.; Thijs, L.; Zwanenburg, B. Solid-phase synthesis of 3,5-disubstituted 1,3-oxazolidin-2-ones by an activation/cyclo-elimination process. Tetrahedron Lett. 1998, 39, 7407–7410.
  • Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides. Eur. J. Org. Chem. 2010, 1875–1884.

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