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Modular syntheses of 1,4,5-trisubstituted 1,2,3-triazoles by a one-pot three-step procedure: toward bio-inspired monomers

  • Annie Praud-Tabariès
  • Olivier Bottzeck
  • Yves BlacheEmail author
Original Paper
  • 15 Downloads

Abstract

Synthesis of 1,4,5-trisubstituted 1H-1,2,3-triazoles is reported by means of a transition metal-catalyzed arylation of 1-substituted-4-(2-bromoethyl)triazoles. The process which consists of one-pot three-step procedure allows a direct access to 1,5-disubstituted-4-(2-hydroxyethyl)triazoles and is suitable as an alternative methodology in the preparation of highly substituted triazoles in view of polymer chemistry.

Graphical abstract

Keywords

1,2,3-Triazole Pd-catalyzed arylation Heck reaction Absorption click chemistry 

Notes

Acknowledgements

This research was supported by the University of Toulon and did not receive any specific grant from other funding agencies (public, or private).

References

  1. 1.
    Hall-Stoodley L, Costerton JW, Stoodley P (2004) Nat Rev Microbiol 2:95CrossRefGoogle Scholar
  2. 2.
    Omae I (2003) Chem Res 103:3431Google Scholar
  3. 3.
    Haras D (2005) Mater Technol 93:27CrossRefGoogle Scholar
  4. 4.
    Qian PY, Lau SCK, Dahms HU, Dobretsov S, Harder T (2007) Marine Biotech 9:399CrossRefGoogle Scholar
  5. 5.
    Linares D, Bottzeck O, Pereira O, Praud-Tabariès A, Blache Y (2011) Bioorg Med Chem Lett 21:6751CrossRefGoogle Scholar
  6. 6.
    Lepoittevin B, Wanga X, Baltaze JP, Liu H, Herry JM, Bellon-Fontaine MN, Roger P (2011) Eur Polym J 47:1842CrossRefGoogle Scholar
  7. 7.
    Liu H, Lepoittevin B, Roddier C, Guerineau V, Bech L, Herry JM, Bellon-Fontaine MN, Roger P (2011) Polymer 52:1908CrossRefGoogle Scholar
  8. 8.
    Hume EBH, Baveja J, Muir B, Schubert TL, Kumar N, Kjelleberg S, Griesser HJ, Thissen H, Read R, Poole-Warren LA, Schindhelm K, Willcox MDP (2004) Biomaterials 25:5023CrossRefGoogle Scholar
  9. 9.
    Peng L, DeSousa J, Su Z, Novak BM, Nevzorov AA, Garland ER, Melander C (2011) Chem Commun 56:4896CrossRefGoogle Scholar
  10. 10.
    Danilovtseva EN, Chafeev MA, Annenkov VV (2012) J Polymer Sci Part A 50:1539CrossRefGoogle Scholar
  11. 11.
    Zhou Z, Li S, Zhang Y, Liu M, Li W (2005) J Am Chem Soc 127:10824CrossRefGoogle Scholar
  12. 12.
    Hetzer M, Chen G, Barner-Kowollik C, Stenzel MH (2010) Macromol Biosci 10:119CrossRefGoogle Scholar
  13. 13.
    Praud A, Bootzeek O, Blache Y (2013) Grenn Chem 15:1138CrossRefGoogle Scholar
  14. 14.
    Zhang W, Chen G, Hu Z, Zhang W, Zhang Z, Zhu XJ (2012) Polym Sci Polym Chem 50:3656CrossRefGoogle Scholar
  15. 15.
    Jin Y, Zhu J, Zhang Z, Cheng Z, Zhang W, Zhu X (2008) Eur Polym J 44:1743CrossRefGoogle Scholar
  16. 16.
    Andjouh S, Bressy C, Blache Y (2015) RSC Adv 6:14496CrossRefGoogle Scholar
  17. 17.
    Chuprakov S, Chernyak N, Dudnik AS, Gevorgyan V (2007) Org Lett 9:2333CrossRefGoogle Scholar
  18. 18.
    Dong JJ, Roger J, Verrier C, Martin T, Le Goff R, Hoarau C, Doucet H (2010) Green Chem 12:2053CrossRefGoogle Scholar
  19. 19.
    Xu HJ, Zhao YQ, Zhou XF (2011) J Org Chem 76:8036CrossRefGoogle Scholar
  20. 20.
    Wang Z, Sheng SR, Wei MH, Liu XL (2016) Synth Commun 46:226CrossRefGoogle Scholar
  21. 21.
    Peterson KP, Larock RC (1998) J Org Chem 63:3185CrossRefGoogle Scholar
  22. 22.
    Nishimura T, Onoue T, Ohe K, Uemura S (1999) J Org Chem 64:6750CrossRefGoogle Scholar
  23. 23.
    Muzart J (2003) Tetrahedron 59:5789CrossRefGoogle Scholar
  24. 24.
    Ackermann L, Ruben V (2009) Org Lett 11:4922CrossRefGoogle Scholar
  25. 25.
    Yamajala KDB, Patil M, Banerjee S (2015) J Org Chem 80:3003CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Université de Toulon, “MAPIEM”ToulonFrance

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