Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®

Journal of Fluorine Chemistry

Volumn 125, Issue 12, 2004, Pages 1939-1945

  Stephens, Chad E ^a   Blake, Jacqueline A ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Fluorination; Heterocycle; Isoxazole; Selectfluor ; Substituent effects; Sulfolane

Indexed keywords

ACETONITRILE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; PYRROLE DERIVATIVE; REAGENT; SELECTIVE ESTROGEN RECEPTOR MODULATOR; SOLVENT;

ARTICLE; FLUORINATION; HIGH TEMPERATURE; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 11444261929     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.08.001     Document Type: Article

References (31)

1. V.S. Parmar, N.K. Sharma, M. Husain, A.C. Watterson, J. Kumar, L.A. Samuelson, A.L. Cholli, A.K. Prasad, A. Kumar, S. Malhotra, N. Kumar, A. Jha, A. Singh, I. Singh, A. Himanshu Vats, N.A. Shakil, S. Trikha, S. Mukherjee, S.K. Sharma, S.K. Singh, A. Kumar, H.N. Jha, C.E. Olsen, C.P. Stove, M.E. Bracke, and M.M. Mareel Bioorg. Med. Chem. 11 2003 913 929
2. B.P. Kansagra, H.H. Bhatt, and A.R. Parikh Indian J. Heterocyclic Chem. 12 2002 61 64
3. R.E. Gershman, E.R. DeSombre, R.N. Hanson, A. Hughes, in: Proceedings of the 224th ACS National Meeting, Boston, MA, 18-22 August 2002 (MEDI-385) (Abstracts).
4. H. Gallardo, C. Zucca, and L. Da Silva Mol. Cryst. Liq. Cryst. 373 2002 181
5. T. Haino, M. Tanaka, K. Ideta, K. Kubo, A. Mori, and Y. Fukazawa Tetrahedron Lett. 45 2004 2277 2279
6. A. Khatyr, H. Maas, and G. Calzaferri J. Org. Chem. 67 2002 6705 6710
7. R.A. Day, J.A. Blake, and C.E. Stephens Synthesis 2003 1586 1590
8. F.M.D. Ismail J. Fluorine Chem. 118 2002 27 33
9. B.E. Smart J. Fluorine Chem. 109 2001 3 11
10. F.C. Krebs, and H. Spanggaard J. Org. Chem. 67 2002 7185 7192
11. C.L. Bumgardner, and J.C. Sloop J. Fluorine Chem. 56 1992 141 146
12. G.S. Lal, G.P. Pez, and R.G. Syvret Chem. Rev. 96 1996 1737 1755
13. S.D. Taylor, C.C. Kotoris, and G. Hum Tetrahedron 55 1999 12431 12477
14. T. Umemoto, S. Fukami, G. Tomizawa, K. Harasawa, K. Kawada, and K. Tomita J. Am. Chem. Soc. 112 1990 8563 8575
15. J.J. Hart, and R.G. Syvret J. Fluorine Chem. 100 1999 157 161
16. K. Adachi, Y. Ohira, G. Tomizawa, S. Ishihara, and S. Oishi J. Fluorine Chem. 120 2003 173 183
17. G.S. Lal J. Org. Chem. 58 1993 2791 2796
18. M. Zupan, J. Iskra, and S. Stavber J. Fluorine Chem. 70 1995 7 8
19. M. Zupan, J. Iskra, and S. Stavber Tetrahedron 52 1996 11341 11348
20. K. Lange, M. Hysell, M. Druelinger, in: Proceedings of the 213th ACS National Meeting, San Francisco, CA, 13-17 April 1997 (CHED-562) (Abstracts).
21. P. Grunanger, and V.-F. Paola Isoxazoles Part 1 1991 Wiley New York
22. R.E. Banks, M.K. Besheesh, R.W. Gorski, N.J. Lawrence, and A.J. Taylor J. Fluorine Chem. 96 1999 129 133
23. P.M. O'Neill, M.D. Tingle, R. Mahmud, R.C. Storr, S.A. Ward, and B.K. Park Bioorg. Med. Chem. Lett. 5 1995 2309 2314
24. T. Fujii, S. Asai, T. Okada, W. Hao, H. Morita, and T. Yoshimura Tetrahedron Lett. 44 2003 6203 6205
25. J.S. Moilliet Industrial routes to ring-fluorinated aromatic compounds R.E. Banks B.E. Smart J.C. Tatlow Organofluorine Chemistry, Principles and Commercial Applications 1994 Plenum Press New York 195 219
26. M. Albert, K. Dax, and J. Ortner Tetrahedron 54 1998 4839 4848
27. S.P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, and C.-H. Wong J. Org. Chem. 64 1999 5264 5279
28. S.D. Sokolov, and N.K. Kochetkov Dokl. Akad. Nauk SSSR 156 1964 1391 (also see [14]; p. 338)
29. A.L. Baumstark, D.R. Chrisope, R.A. Keel, and D.W. Boykin J. Heterocyclic Chem. 17 1980 1719 1721
30. D.R. Chrisope, R.A. Keel, A.L. Baumstark, and D.W. Boykin J. Heterocyclic Chem. 18 1981 795 798
31. S.K. Kotovskaya, S.A. Romanova, V.N. Charushin, M.I. Kodess, and O.N. Chupakhin J. Fluorine Chem. 125 2004 421 428