Synthesis of 5-halogenated 1,2,3-triazoles under stoichiometric Cu(I)-mediated azide-alkyne cycloaddition (CuAAC or 'Click Chemistry')

Carbohydrate Research

Volumn 362, Issue , 2012, Pages 79-83

  Goyard, David ^a   Praly, Jean Pierre ^a   Vidal, Sébastien ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

1,2,3 Triazole; 1,3 Dipolar cycloaddition; Atropoisomer; Catalysis; Click Chemistry

Indexed keywords

1 ,2 ,3-TRIAZOLES; 1 ,3-DIPOLARCYCLOADDITION; 1,2,3-TRIAZOLE; ADDITIONAL STRUCTURES; ATROPOISOMER; AZIDE-ALKYNE CYCLOADDITION; BIO-MOLECULAR; CLICK CHEMISTRY; COPPER HALIDE; CRYSTALLOGRAPHIC DATA; GLYCOGEN PHOSPHORYLASE; HETEROCYCLES; POTENT INHIBITOR; TRIAZOLE RING; TYPE-2 DIABETES;

ACETYLENE; CATALYSIS; COPPER COMPOUNDS; CYCLOADDITION; HALOGENATION; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

IODINE;

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE DERIVATIVE; AZIDE; COPPER; COPPER CHLORIDE; HALIDE;

ARTICLE; CHEMICAL ANALYSIS; CLICK CHEMISTRY; CRYSTALLOGRAPHY; CYCLOADDITION; PRIORITY JOURNAL; STOICHIOMETRY; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; CLICK CHEMISTRY; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; ENZYME INHIBITORS; GLYCOGEN PHOSPHORYLASE; HALOGENATION; HUMANS; HYPOGLYCEMIC AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIAZOLES;

EID: 84867608943     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.08.014     Document Type: Article

References (29)

1. L. Agius Best Pract. Res. Clin. Endocrinol. Metab. 21 2007 587 605
2. N.G. Oikonomakos, and L. Somsák Curr. Opin. Invest. Drugs 9 2008 379 395
3. J.-P. Praly, and S. Vidal Mini-Rev. Med. Chem. 10 2010 1102 1126
4. L. Somsák, K. Czifrák, M. Tóth, E. Bokor, E.D. Chrysina, K.M. Alexacou, J.M. Hayes, C. Tiraidis, E. Lazoura, D.D. Leonidas, S.E. Zographos, and N.G. Oikonomakos Curr. Med. Chem. 15 2008 2933 2983
5. É. Bokor, T. Docsa, P. Gergely, and L. Somsák Bioorg. Med. Chem. 18 2010 1171 1180
6. E.D. Chrysina, É. Bokor, K.-M. Alexacou, M.-D. Charavgi, G.N. Oikonomakos, S.E. Zographos, D.D. Leonidas, N.G. Oikonomakos, and L. Somsák Tetrahedron: Asymmetry 20 2009 733 740
7. R. Huisgen, G. Szeimies, and L. Möbius Chem. Ber. 100 1967 2494 2507
8. M. Meldal, and C.W. Tornoe Chem. Rev. 108 2008 2952 3015
9. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
10. C.W. Tornoe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
11. A. Dondoni Chem. Asian J. 2 2007 700 708
12. A.R. Bogdan, and K. James Org. Lett. 13 2011 4060 4063
13. J.E. Hein, J.C. Tripp, L.B. Krasnova, K.B. Sharpless, and V.V. Fokin Angew. Chem., Int. Ed. 48 2009 8018 8021
14. M. Juricek, K. Stout, P.H.J. Kouwer, and A.E. Rowan Org. Lett. 13 2011 3494 3497
15. B.H.M. Kuijpers, G.C.T. Dijkmans, S. Groothuys, P.J.L.M. Quaedflieg, R.H. Blaauw, F.L. van Delft, and F.P.J.T. Rutjes Synlett 2005 3059 3062
16. J.M. Schulman, A.A. Friedman, J. Panteleev, and M. Lautens Chem. Commun. 48 2012 55 57
17. C. Spiteri, and J.E. Moses Angew. Chem., Int. Ed. 49 2010 31 33
18. P. Diner, T. Andersson, J. Kjellen, K. Elbing, S. Hohmann, and M. Grotli New J. Chem. 33 2009 1010 1016
19. V. Malnuit, M. Duca, A. Manout, K. Bougrin, and R. Benhida Synlett 2009 2123 2126
20. N.W. Smith, B.P. Polenz, S.B. Johnson, and S.V. Dzyuba Tetrahedron Lett. 51 2010 550 553
21. Y.-M. Wu, J. Deng, Y. Li, and Q.-Y. Chen Synthesis 2005 1314 1318
22. B. Gerard, J. Ryan, A.B. Beeler, and J.A. Porco Jr. Tetrahedron 62 2006 6405 6411
23. J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302 1315
24. Y. Angell, and K. Burgess Angew. Chem., Int. Ed. 46 2007 3649 3651
25. X. Chen, G.N. Khairallah, R.A.J. O'Hair, and S.J. Williams Tetrahedron Lett. 52 2011 2750 2753
26. J. González, V.M. Pérez, D.O. Jiménez, G. Lopez-Valdez, D. Corona, and E. Cuevas-Yañez Tetrahedron Lett. 52 2011 3514 3517
27. M. Kwon, Y. Jang, S. Yoon, D. Yang, and H.B. Jeon Tetrahedron Lett. 53 2012 1606 1609
28. I.K. Mati, and S.L. Cockroft Chem. Soc. Rev. 39 2010 4195 4205
29. M. Berthod, G. Mignani, G. Woodward, and M. Lemaire Chem. Rev. 105 2005 1801 1836