Advertisement

Journal of Flow Chemistry

, Volume 5, Issue 3, pp 142–144 | Cite as

Efficient Continuous-Flow Synthesis of Macrocyclic Triazoles

  • Anne-Catherine Bédard
  • Jeffrey Santandrea
  • Shawn K. Collins
Communication
  • 14 Downloads

Abstract

The continuous-flow synthesis of a series of 11- to 26-membered macrocycles via copper-catalyzed azide-alkyne cycloaddition is reported. The approach employs homogeneous catalysis to promote formation of triazole-containing macrocycles in good to excellent yields (65–90%) at relatively high concentration (30–50 mM) using a phase separation strategy.

Keywords

macrocycle click copper 

Supplementary material

41981_2015_5030142_MOESM1_ESM.pdf (494 kb)
Supplementary material, approximately 506 KB.

References

  1. 1.
    (a) Driggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. Nat. Rev. Drug Discovery 2008, 7, 608–624CrossRefGoogle Scholar
  2. (b).
    Marsault, E.; Peterson, M. L. J. Med. Chem. 2011, 54, 1961–2004CrossRefGoogle Scholar
  3. (c).
    Yudin, A. K. Chem. Sci. 2015, 6, 30–49.CrossRefGoogle Scholar
  4. 2.(a)
    Bédard, A.-C.; Regnier, S.; Collins, S. K., Green Chem. 2013, 15, 1962–1966CrossRefGoogle Scholar
  5. (b).
    Bogdan, A. R.; James, K. Org. Lett. 2011, 13, 4060–4063.CrossRefGoogle Scholar
  6. 3. (a)
    Bogdan, A. R.; Jerome, S. V.; Houk, K. N.; James, K. J. Am. Chem. Soc. 2012, 134, 2127–2138CrossRefGoogle Scholar
  7. (b).
    Bogdan, A. R.; James, K. Chem.–Eur. J. 2010, 16, 14506–14512.CrossRefGoogle Scholar
  8. 4.
    Bédard, A.-C.; Collins, S. K., J. Am. Chem. Soc. 2011, 133, 19776–19981.CrossRefGoogle Scholar
  9. 5. (a)
    Pasini, D. Molecules 2013, 18, 9512–9530CrossRefGoogle Scholar
  10. (b).
    Caricato, M.; Olmo, A.; Gargiulli, C.; Gattuso, G.; Pasini, D. Tetrahedron 2012, 68, 7861–7866CrossRefGoogle Scholar
  11. (c).
    Yongjun Li, Y.; Flood, A. H. Angew. Chem., Int. Ed. 2008, 47, 2649–2652.CrossRefGoogle Scholar
  12. 6. (a)
    Jogula, S.; Dasari, B.; Khatravath, M.; Chandrasekar, G.; Kitambi, S. S.; Arya, P. Eur. J.Org. Chem. 2013, 5036–5040Google Scholar
  13. (b).
    Potopnyk, M. A.; Jarosz, S. in Click Chemistry in Glycoscience; Witczak, Z. J., Bielski, R., Eds.; John Wiley & Sons, Inc., Hoboken, New Jersey, 2013; 235.CrossRefGoogle Scholar
  14. 7. (a)
    Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128–1137CrossRefGoogle Scholar
  15. (b).
    Whiting, M.; Tripp, J. C.; Lin, Y. C.; Lindstrom, W.; Olson, A. J.; Elder, J. H.; Sharpless, K. B.; Fokin, V. V. J. Med. Chem. 2006, 49, 7697–7710CrossRefGoogle Scholar
  16. (c).
    Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Poulsen, S.-A. in Drug Design Research Perspectives; Kaplan, S. P., Ed.; Nova, Hauppauge, 2007; 57Google Scholar
  17. (d).
    Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192–3193.CrossRefGoogle Scholar
  18. 8. (a)
    Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596–2599CrossRefGoogle Scholar
  19. (b).
    Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057–3064.CrossRefGoogle Scholar
  20. 9.
    Bédard, A.-C.; Collins, S. K., Org. Lett. 2014, 16, 5286–5289.CrossRefGoogle Scholar
  21. 10. (a)
    Schulman, J. M.; Friedman, A. A.; Panteleev, J.; Lautens, M. Chem. Commun. 2012, 48, 55–57CrossRefGoogle Scholar
  22. (b).
    Deng, J.; Wu, Y.-M.; Chen, Q.-Y. Synthesis 2005, 16, 2730–2738Google Scholar
  23. (c).
    Worrell, B. T.; Hein, J. E.; Fokin, V. V. Angew. Chem., Int. Ed. 2012, 51, 11791–11794.CrossRefGoogle Scholar
  24. 11. (a)
    Henning S. G. Beckmann, H. S. G.; Niel, F.; Hagerman, C. E.; Johansson, H.; Tan, Y. S.; Wilcke, D.; Spring, D. R. Nature Chem. 2013, 5, 861–867CrossRefGoogle Scholar
  25. (b).
    Bauer, R. A.; Wenderski, T. A.; Tan, D. S. Nature Chem. Biol. 2013, 9, 21–29CrossRefGoogle Scholar
  26. (c).
    Kopp, F.; Stratton, C. F.; Akella, L. B.; Tan, D. S. Nature Chem. Biol. 2012, 8, 358–365.CrossRefGoogle Scholar
  27. 12.
    Bédard, A.-C.; Collins, S. K. Chem. Commun. 2012, 48, 6420–6422.CrossRefGoogle Scholar

Copyright information

© Akadémiai Kiadó 2015

Authors and Affiliations

  • Anne-Catherine Bédard
    • 1
  • Jeffrey Santandrea
    • 1
  • Shawn K. Collins
    • 1
  1. 1.Department of Chemistry and Centre for Green Chemistry and CatalysisUniversité de MontréalMontréalCanada

Personalised recommendations