Chemoselective preparation of disymmetric bistriazoles from bisalkynes

Tetrahedron Letters

Volumn 52, Issue 6, 2011, Pages 658-660

  Elamari, Hichem ^a,b   Meganem, Faouzi ^b   Herscovici, Jean ^a   Girard, Christian ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b University of Carthage   (Tunisia)

Author keywords

Activation; Alkyne; Azide; Click chemistry; Huisgen's reaction

Indexed keywords

ALKYNE; COPPER; POLYMER; TRIAZOLE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLOADDITION; HUISGEN REACTION; ISOMER; MOLECULE; OXIDATION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 79251595172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.141     Document Type: Article

References (33)

1. R. Huisgen Angew. Chem. 75 1963 604 637
2. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598
3. R. Huisgen A. Padwa, 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 Wiley-Interscience New York 1 176
4. C.W. Tornøe, and M. Meldal M. Lebl, R.A. Houghten, 17th American Peptides Symposium Proceedings Book. Peptides: The Wave of the Future 2001 American Peptide Society and Kluwer Academic San Diego 263 264
5. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
6. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem. 114 2002 2708 2711
7. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
8. For reviews see: V.D. Bock, H. Hiemstra, and J.H. van Maarseveen Eur. J. Org. Chem. 2006 51 68
9. P. Wu, and V.V. Fokin Aldrichim. Acta 40 2007 7 17
10. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952 3015
11. M. Meldal Macromol. Rapid Commun. 29 2008 1016 1051
12. F. Amblard, J.H. Cho, and R.F. Schinazi Chem. Rev. 109 2009 4207 4220
13. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem. 113 2001 2056 2075
14. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
15. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128 1137
16. J.E. Moses, and A.D. Moorhouse Chem. Soc. Rev. 36 2007 1249 1262
17. Special Issue - Click Chemistry. QSAR Comb. Sci. 2007, 26, 1111-1326.
18. R.K. Iha, K.L. Wooley, A.M. Nyström, D.J. Burke, M.J. Kade, and C. Hawker J. Chem. Rev. 109 2009 5620 5686
19. Special Issue - Click Chemistry. Chem. Soc. Rev. 2010, 39, 1231-1405.
20. F. Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B. Sharpless, and V.V. Fokin J. Am. Chem. Soc. 127 2005 210 216
21. V.O. Rodionov, V.V. Fokin, and M.G. Finn Angew. Chem., Int. Ed. 44 2005 2210 2215 See also Ref. 2f,g.
22. C. Girard, E. Önen, M. Aufort, S. Beauvire, E. Samson, and J. Herscovici Org. Lett. 8 2006 1689 1692
23. I. Jlalia, H. Elamari, F. Meganem, J. Herscovici, and C. Girard Molecules 14 2009 528 539
24. I. Jlalia, C. Beauvineau, S. Beauvire, E. Önen, M. Aufort, A. Beauvineau, E. Khaba, J. Herscovici, F. Meganem, and C. Girard Molecules 15 2010 3087 3120
25. For the higher reactivity of methyl propiolate, see: K.R. Reddy, K. Rajgopal, and M.L. Kantam Synlett 2006 957 959
26. I. Jlalia, H. Elamari, F. Meganem, J. Herscovici, and C. Girard Tetrahedron Lett. 49 2008 6756 6758
27. N.J. Agard, J.A. Prescher, and C.R. Bertozzi J. Am. Chem. Soc. 126 2004 15046 15047
28. J.M. Baskin, J.A. Prescher, S.T. Laughlin, N.J. Agard, P.V. Chang, I.A. Miller, A. Lo, J.A. Codelli, and C.R. Bertozzi PNAS 104 2007 16793 16797
29. V. Aucagne, and D.A. Leigh Org. Lett. 8 2006 4505 4507
30. V. Fiandanese, D. Bottalico, G. Marchese, A. Punzi, and F. Capuzzolo Tetrahedron 65 2009 10573 10580
31. O.D. Montagnat, G. Lessene, and A.B. Hughes J. Org. Chem. 75 2010 390 398
32. J.M. Aizpurua, I. Azcune, R.M. Fratila, E. Balentova, M. Sagartzazu-Aizpurua, and J.I. Miranda Org. Lett. 12 2010 1584 1587
33. 2 (2 × 1 mL). Evaporation of the solvent gave the corresponding bistriazole 4-6 (9 or 10).