A new solvent system for efficient synthesis of 1,2,3-triazoles

Tetrahedron Letters

Volumn 47, Issue 29, 2006, Pages 5105-5109

  Lee, Bo Young ^a   Park, So Ra ^a   Jeon, Heung Bae ^a   Kim, Kwan Soo ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE; AZIDE; CARBON 11; COPPER; HYDROGEN; SOLVENT; WATER;

ARTICLE; CATALYSIS; CYCLOADDITION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 33744966628     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.079     Document Type: Article

References (30)

1. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057
2. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596
3. Billing J.F., and Nilsson U.J. J. Org. Chem. 70 (2005) 4847
4. van Maarseveen J.H., Horne W.S., and Ghadiri M.R. Org. Lett. 7 (2005) 4503
5. Bodine K.D., Gin D.Y., and Gin M.S. Org. Lett. 7 (2005) 4479
6. Zhou Z., and Fahrni C.J. J. Am. Chem. Soc. 126 (2004) 8862
7. Jin T., Kamijo S., and Yamamoto Y. Eur. J. Org. Chem. (2004) 3789
8. Bodine K.D., Gin D.Y., and Gin M.S. J. Am. Chem. Soc. 126 (2004) 1638
9. Seo T.S., Li Z., Ruparel H., and Ju J. J. Org. Chem. 68 (2003) 609
10. Fazio F., Bryan M.C., Blixt O., Paulson J.C., and Wong C.-H. J. Am. Chem. Soc. 124 (2002) 14397
11. Speers A.E., and Cravatt B.F. Chem. Biol. 11 (2004) 535
12. Deiters A., Cropp T.A., Mukherji M., Chin J.W., Anderson J.C., and Schultz P.G. J. Am. Chem. Soc. 125 (2003) 11782
13. Link A.J., and Tirrell D.A. J. Am. Chem. Soc. 125 (2003) 11164
14. Lee L.V., Mitchell M.L., Huang S.-J., Fokin V.V., Sharpless K.B., and Wong C.-H. J. Am. Chem. Soc. 125 (2003) 9588
15. Speers A.E., Adam G.C., and Cravatt B.F. J. Am. Chem. Soc. 125 (2003) 4686
16. Wang Q., Chan T.R., Hilgraf R., Fokin V.V., Sharpless K.B., and Finn M.G. J. Am. Chem. Soc. 125 (2003) 3192
17. Breinbauer R., and Kohn M. ChemBioChem 4 (2003) 1147
18. Diaz D.D., Punna S., Holzer P., McPherson A.K., Sharpless K.B., Fokin V., and Finn M.G. J. Polym. Sci. Part A 42 (2004) 4392
19. Wu P., Feldman A.K., Nugent A.K., Hawker C.J., Scheel A., Voit B., Pyun J., Fréchet J.M.J., Sharpless K.B., and Fokin V.V. Angew. Chem., Int. Ed. 43 (2004) 3928
20. Lee J.K., Chi Y.S., and Choi I.S. Langmuir 20 (2004) 3844
21. Collman J.P., Devaraj N.K., and Chidsey C.E.D. Langmuir 20 (2004) 1051
22. Lober S., Rodriguez-Loaiza P., and Gmeiner P. Org. Lett. 5 (2003) 1753
23. Genin M.J., Allwine D.A., Anderson D.J., Barbachyn M.R., Emmert D.E., Garmon S.A., Graber D.R., Grega K.C., Hester J.B., Hutchinson D.K., Morris J., Reischer R.D., Stper D., and Yagi B.H. J. Med. Chem. 43 (2000) 953
24. Wamhoff H. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry (1984), Pergamon, Oxford 669-732
25. Buckle D.R., Rockell C.J.M., Smith H., and Spicer B.A. J. Med. Chem. 29 (1986) 2262
26. Alvarez R., Velazquez S., San-Felix A., Aquaro S., De Clercq E., Perno C.-F., Karlsson A., Balzarini J., and Camarasa M.J. J. Med. Chem. 37 (1994) 4194
27. Meng J.-C., Fokin V.V., and Finn M.G. Tetrahedron Lett. 46 (2005) 4543
28. Chan T.R., Hilgraf R., Sharpless K.B., and Fokin V.V. Org. Lett. 6 (2004) 2853
29. 4, and concentrated. The residue was purified by flash column chromatography (hexane/EtOAc, 2:1) to give 1,2,3-triazole 16 (170 mg, 97%) as a white solid.
30. Katritzky A.R., and Singh S.K. J. Org. Chem. 67 (2002) 9077