X. Chen et al. / Tetrahedron Letters 52 (2011) 2750–2753
2753
15. Schade, M. A.; Fleckenstein, J. E.; Knochel, P.; Koszinowski, K. J. Org. Chem. 2010,
75, 6848–6857.
Acknowledgments
16. Vikse, K. L.; Henderson, M. A.; Oliver, A. G.; McIndoe, J. S. Chem. Commun. 2010,
46, 7412–7414.
Funding support was provided by the Australian Research
Council, including via the Centre of Excellence for Free Radical
Chemistry and Biotechnology. S. Vergunst is thanked for technical
support. M. G. Finn is acknowledged for the gift of THPTA.
17. Lamari, F. N.; Kuhn, R.; Karamanos, N. K. J. Chromatogr., B 2003, 793, 15–36.
18. Suzuki, S.; Kakehi, K.; Honda, S. Anal. Chem. 1996, 68, 2073–2083.
19. Unterieser, I.; Mischnick, P. Carbohydr. Res. 2010, 346, 68–75.
20. Roth, K. D. W.; Huang, Z.-H.; Sadagopan, N.; Watson, J. T. Mass Spectrom. Rev.
1999, 17, 255–274.
21. Despite considerable effort, we were not successful in isolating a pure sample
of the 5-hydroxytriazole for detailed structural characterization via other
Supplementary data
spectroscopic techniques. 5-Hydroxytriazoles are in equilibrium with
a-
diazoamides and we speculate that these electron-deficient amides undergo
facile hydrolysis. See: Lobodin, V. V.; Morzherin, Y. Y.; Blumenthal, T.; Bilusich,
D.; Ovcharenko, V. V.; Bowie, J. H.; Lebedev, A. T. Arkivoc 2005, 5, 189–198.
22. Hong, V.; Presolski, S. I.; Ma, C.; Finn, M. G. Angew. Chem., Int. Ed. 2009, 48,
9879–9883.
23. Khossravi, M.; Borchardt, R. T. Pharm. Res. 1998, 15, 1096–1102.
24. Taqui Khan, M. M.; Martell, A. E. J. Am. Chem. Soc. 1967, 89, 4176–4185.
25. Hong, V.; Steinmetz, N. F.; Manchester, M.; Finn, M. G. Bioconjug. Chem. 2010,
21, 1912–1916.
26. Sen Gupta, S.; Kuzelka, J.; Singh, P.; Lewis, W. G.; Manchester, M.; Finn, M. G.
Bioconjug. Chem. 2005, 16, 1572–1579.
27. Soriano Del Amo, D.; Wang, W.; Jiang, H.; Besanceney, C.; Yan, A. C.; Levy, M.;
Liu, Y.; Marlow, F. L.; Wu, P. J. Am. Chem. Soc. 2010, 132, 16893–16899.
28. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am.
Chem. Soc. 2003, 125, 3192–3193.
Supplementary data associated with this article can be found, in
References and notes
1. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302–1315.
2. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952–3015.
3. Wu, P.; Fokin, V. V. Aldrichim. Acta 2007, 40, 7–17.
4. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2005, 51–68.
5. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed.
2002, 41, 2596–2599.
6. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057–3064.
7. Dedola, S.; Nepogodiev, S. A.; Field, R. A. Org. Biomol. Chem. 2007, 5, 1006–1017.
8. Evans, R. A. Aust. J. Chem. 2007, 60, 384–395.
9. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A.
Med. Res. Rev. 2008, 28, 278–308.
29. Krasin´ ski, A.; Fokin, V. V.; Sharpless, K. B. Org. Lett. 2004, 6, 1237–1240.
30. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853–
2855.
31. Donnelly, P. S.; Zanatta, S. D.; Zammit, S. C.; White, J. M.; Williams, S. J. Chem.
Commun. 2008, 2459–2461.
10. Best, M. D. Biochemistry 2009, 48, 6571–6584.
11. Angell, Y.; Burgess, K. Angew. Chem., Int. Ed. 2007, 46, 3649–3651.
12. Gerard, B.; Ryan, J.; Beeler, A. B.; Porco, J. A., Jr. Tetrahedron Lett. 2006, 62, 6405–
6411.
13. Chisholm, D. M.; McIndoe, J. S. Dalton Trans. 2008, 3933–3945.
14. Koszinowski, K. J. Am. Chem. Soc. 2010, 132, 6032–6040.
32. Kuang, G. C.; Michaels, H. A.; Simmons, J. T.; Clark, R. J.; Zhu, L. J. Org. Chem.
2010, 75, 6540–6548.