β-Tosylethylazide: a useful synthon for preparation of N-protected 1,2,3-triazoles via click chemistry

Tetrahedron Letters

Volumn 47, Issue 18, 2006, Pages 3035-3038

  Yap, Amy H ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

1,2,3 Triazoles; 1,3 Dipolar cycloadditions; Nitrogen heterocycles; Protecting groups

Indexed keywords

BETA TOSYLETHYLAZIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHROMATOGRAPHY; CYCLOADDITION; PURIFICATION; SYNTHESIS;

EID: 33645880449     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.020     Document Type: Article

References (30)

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9. For reviews of 'click chemistry' see:. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004
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19. For other examples of synthesis of N-protected 1,2,3-triazoles via 1,3-dipolar cycloadditions with alkynes see:. Kamijo S., Huo Z., Jin T., Kanazawa C., and Yamamoto Y. J. Org. Chem. 70 (2005) 6389
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24. 3.
25. +), found 226.0643.
26. 2O, and was dried in vacuo.
27. We thank Dr. Hemant Yennawar (Penn State Small Molecule X-Ray Crystallographic Facility) for this crystal structure determination. CCDC 600036 contains the supplementary crystallographic data, which can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
28. General deprotection procedure. A solution of t-BuOK in THF (1.0 M, 0.86 mL) was slowly added to a solution of protected triazole (200 μmol) in THF (10 mL) at -78 °C. The solution was slowly warmed to 0 °C over a period of 1-3 h. The reaction mixture was neutralized with glacial acetic acid (24.7 μL, 100 μmol) at 0 °C. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography (30:70 EtOAc/hexanes) to afford the deprotected 1,2,3-triazole.
29. Zhang L., Chen X., Xue P., Sun H.H.Y., Williams I.D., Sharpless K.B., Fokin V.V., and Jia G. J. Am. Chem. Soc. 127 (2005) 15998
30. 2 (0.04 g, 0.05 mmol) in benzene (2.5 mL). The reaction mixture was stirred and heated at reflux for 2 h. After cooling the mixture to rt, the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica gel (50:50 ether/hexanes to 100% ether gradient) to yield the TSE-protected 1,2,3-triazole.