Study on the reactions of fluoroalkanesulfonyl azides with N-alkylindoles

Journal of Fluorine Chemistry

Volumn 125, Issue 10, 2004, Pages 1529-1536

  He, Ping ^a   Zhu, Shi Zheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,3 Dipolar cycloaddition; Carbanion process; Diazo transfer; Fluoroalkanesulfonyl azides; N alkylindoles

Indexed keywords

1,4 DIOXANE DERIVATIVE; AZIDE; FLUORINE DERIVATIVE; INDOLE DERIVATIVE; ORGANIC SOLVENT;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG DISTRIBUTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 4644363243     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.06.003     Document Type: Article

References (28)

1. Garg N.K. Sarpong R. Stoltz B.M. J. Am. Chem. Soc. 124 2002 13179-13184
2. Pirrung M.C. Li Z. Park K. Zhu J. J. Org. Chem. 67 2002 7919-7926
3. Wilkie G.D. Elliot G.I. Blagg B.S.J. Wolkenberg S.E. Soenen D.R. Miller M.M. Pollack S. Boger D.L. J. Am. Chem. Soc. 124 2002 11292-11294
4. Dow R.L. Schneider S.R. Paight E.S. Hank R.F. Chiang P. Cornelius P. Lee E. Newsome W.P. Swick A.G. Spitzer J. Hargrowe D.M. Bioorg. Med. Chem. Lett. 3 2003 379-382
5. Madsen P. Ling A. Plewe M. Sams C.K. Knudsen L.B. Sidelmann U.G. Ynddal L. Brand C.L. Andersen B. Murphy D. Teng M. J. Med. Chem. 45 2002 5755-5775
6. Della S.G. Capozzo D. Izzo I. Giordano A. Iommazzo A. Spinella A. Tetrahedron Lett. 43 2002 8839-8841
7. Lynch S.M. Bur S.K. Padwa A. Organic Lett. 4 2002 4643-4645
8. Yang C.G. Liu G. Jiang B. J. Org. Chem. 67 2002 9392-9396
9. Fusco R. Bianchetti G. Rossi S. Gazz. Chim. Ital. 91 1961 933-957
10. Bailey A.S. Churn M.C. Wedgwood J.J. Tetrahedron Lett. 13 1968 5953-5954
11. A.S. Bailey, J.J. Merer, J. Chem. Soc.(C). (1966) 1345-1348
12. A.S. Bailey, W.A. Warr, G.B. Allison, C.K. Prout, J. Chem. Soc.(C). (1970) 956-964
13. Bailey A.S. Scattergood R. Warr W.A. Tetrahedron Lett. 15 1970 2979-2982
14. P. V. Ramachandran. In: Proceedings of Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions; ACS Symposium Series 746, Washington, DC, 2000
15. I. Ojima, J. R. McCarthy, J. T. Welch. In: Proceedings of Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639, Washington, DC, 1996
16. V.P. Kukhar', V.A. Soloshonok. In: Proceedings of Fluorine-containing Amino Acids: Synthesis and Properties. Wiley, New York, 1995
17. J.T. Welch. In: Proceedings of Selective Fluorination in Organic and Bioorganic Chemistry; ACS symposium series 456, Washington, DC, 1991
18. J.T. Welth, S. Eswarakrishnan. In : Proceedings of Fluorine in Bioorganic Chemistry, Wiley-Interscience, John Wiley & Sons, 1991.
19. Xu Y. Wang Y.L. Zhu S.Z. J. Fluorine Chem. 104 2000 195-200
20. Xu Y. Zhu S.Z. Tetrahedron 57 2001 669-674
21. Zhu S.Z. Jin G.F. Zhao J.W. J. Fluorine Chem. 120 2003 65-69
22. M. Regitz, Synthesis, 1972, 351-373.
23. Abramovitch R.A. Takaya T. J. Org. Chem. 37 1972 2022-2029
24. Harmon R.E. Wellman G. Gupta S.K. J. Org. Chem. 38 1973 11-16
25. Bailey A.S. Buckley A.J. Warr W.A. J. Chem. Soc. Perkin Trans. 1 1972 1626-1629
26. R.E. Harmon, G. Wellman, S.K. Gupta, J. Chem. Soc. Chem. Commun. 1972, pp. 1191-1192.
27. Zhu S.Z. Tetrahedron Lett. 33 1992 6503-6504
28. Kikugawa Y. Miyake Y. Synthesis 6 1981 461-462