Bulletin of the Korean Chemical Society

  • 제31권7호
  • /
  • Pages.1843-1847
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Azide/Alkyne Resins for Quick Preparation of 1,4-Disubstituted 1,2,3-Triazoles

  • 투고 : 2009.10.14
  • 심사 : 2009.11.16
  • 발행 : 2010.07.20
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초록

An efficient method for the preparation of 1,4-disubstituted 1,2,3-triazole compounds is described using polymeric quaternary ammonium salts having azide or alkyne functionality to remove unreacted excess starting molecules (azide/alkyne). Copper metal could easily be removed by simple filtration with a short $Na_2SO_4$/silica cartridge, affording highly regioselective products in high yield and excellent purity without the need for work-up, extraction and chromatographic purification.

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참고문헌

  1. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057. https://doi.org/10.1021/jo011148j
  2. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
  3. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596. https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  4. Ng, S. L.; Yang, P.-Y.; Chen, K. Y.-T.; Srinivasan, R.; Yao, S. Q. Org. Biomol. Chem. 2008, 6, 844. https://doi.org/10.1039/b718304f
  5. Chen, J.; Nikolovska-Coleska, Z.; Yang, C. Y.; Gomez, C.; Gao, W.; Krajewski, K.; Jiang, S.; Roller, P.; Wang, S. Bioorg. Med. Chem. Lett. 2007, 17, 3939. https://doi.org/10.1016/j.bmcl.2007.04.096
  6. Geng, J.; Mantovani, G.; Tao, L.; Nicolas, J.; Chen, G.; Wallis, R.; Mitchell, D. A.; Johnson, B. R. G.; Evans, S. D.; Haddleton, D. M. J. Am. Chem. Soc. 2007, 129, 15156. https://doi.org/10.1021/ja072999x
  7. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. https://doi.org/10.1021/ja021381e
  8. Qin, A.; Jim, C. K. W.; Lu, W.; Lam, J. W. Y.; Häussler, M.; Dong, Y.; Sung, H. H. Y.; Williams, I. D.; Wong, G. K. L.; Tang, B. Z. Macromolecules 2007, 40, 2308. https://doi.org/10.1021/ma062859s
  9. Lee, J. W.; Han, S. C.; Kim, J. H.; Ko, Y. H.; Kim, K. Bull. Korean Chem. Soc. 2007, 28, 1837. https://doi.org/10.5012/bkcs.2007.28.10.1837
  10. Lee, J. W.; Kim, B.-K.; Jin, S.-H. Bull. Korean Chem. Soc. 2005, 26, 833. https://doi.org/10.5012/bkcs.2005.26.5.833
  11. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Fréchet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928. https://doi.org/10.1002/anie.200454078
  12. Li, Z.-B.; Wu, Z.; Chen, K.; Chin, F. T.; Chen, X. Bioconjugate Chem. 2007, 18, 1987. https://doi.org/10.1021/bc700226v
  13. Sirion, U.; Kim, H. J.; Lee, J. H.; Seo, J. W.; Lee, B. S.; Lee, S. J.; Oh, S. J.; Chi, D. Y. Tetrahedron Lett. 2007, 48, 3953. https://doi.org/10.1016/j.tetlet.2007.04.048
  14. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128. https://doi.org/10.1016/S1359-6446(03)02933-7
  15. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Medicinal Research Reviews 2008, 28, 278. https://doi.org/10.1002/med.20107
  16. Brik, A.; Alexandratos, J.; Lin, Y. C.; Elder, J. H.; Olson, A. J.; Wlodawer, A.; Goodsell, D. S.; Wong C. H. ChemBioChem 2005, 6, 1167. https://doi.org/10.1002/cbic.200500101
  17. Angell, Y.; Burgess, K. J. Org. Chem. 2005, 70, 9595. https://doi.org/10.1021/jo0516180
  18. Bock, V. D.; Speijer, D.; Hiemstra, H.; van Maarseveen, J. H. Org. Biomol. Chem. 2007, 5, 971. https://doi.org/10.1039/b616751a
  19. Hitotsuyanagi, Y.; Motegi, S.; Hasuda, T.; Takeya, K. Org. Lett. 2004, 6, 1111. https://doi.org/10.1021/ol040005r
  20. Horne, W. S.; Stout, C. D.; Ghadiri, M. R. J. Am. Chem. Soc. 2003, 125, 9372. https://doi.org/10.1021/ja034358h
  21. Horne, W. S.; Yadav, M. K.; Stout, C. D.; Ghadiri, M. R. J. Am. Chem. Soc. 2004, 126, 15366. https://doi.org/10.1021/ja0450408
  22. Girard, C.; Önen, E.; Aufort, M.; Beauvière, S.; Samson, E.; Herscovici, J. Org. Lett. 2006, 8, 1689. https://doi.org/10.1021/ol060283l
  23. Sirion, U.; Bae, Y. J.; Lee, B. S.; Chi, D. Y. Synlett 2008, 2326.
  24. Smith, C. D.; Baxendale, I. R.; Lanners, S.; Hayward, J. J.; Smith, S. C.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 1559. https://doi.org/10.1039/b702995k
  25. Lee, B. S.; Mahajan, S.; Janda, K. D. Tetrahderon Lett. 2005, 46, 807. https://doi.org/10.1016/j.tetlet.2004.12.013
  26. Tregre, G. J.; Mathias, L. J. J. Polym. Sci. Pol. Chem. 1997, 35, 587. https://doi.org/10.1002/(SICI)1099-0518(199702)35:3<587::AID-POLA25>3.0.CO;2-J

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