Syntheses of new difluoromethylene benzoxazole and 1,2,4-oxadiazole derivatives, as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

Journal of Fluorine Chemistry

Volumn 126, Issue 4, 2005, Pages 533-540

  Medebielle, Maurice ^a,b   Ait Mohand, Samia ^a   Burkhloder, Conrad ^c   Dolbier Jr , William R ^c   Laumond, Géraldine ^d   Aubertin, Anne Marie ^d  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITÉ LYON 1   (France)

^c UNIVERSITY OF FLORIDA   (United States)

^d UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

1,2,4 Oxadiazole; Benzoxazole; Dehydroxylation; Difluoromethyl heterocycles; Fluorination; HIV; Oxidation

Indexed keywords

EID: 23244460976     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.12.016     Document Type: Article

References (26)

1. J.S. Wai, T.M. Williams, D.L. Bamberger, T.E. Fisher, J.M. Hoffman, R.J. Hudcosky, S.C. MacTough, C.S. Rooney, W.S. Saari, C.M. Thomas, M.E. Goldman, J.A. O'Brien, E.A. Emini, J.H. Nunberg, J.C. Quintero, W.A. Schleif, and P.S. Anderson J. Med. Chem. 36 1993 249
2. M. Médebielle, M.A. Oturan, J. Pinson, and J-M. Savéant J. Org. Chem. 61 1996 1331
3. M. Médebielle, J. Pinson, and J-M. Savéant Electrochim. Acta 42 1997 2049
4. S. Fujii, K. Kato, and M. Médebielle Tetrahedron 56 2000 2655
5. C. Burkholder, W.R. Dolbier Jr., S. Ait-Mohand, and M. Médebielle Tetrahedron Lett. 42 2001 3077
6. W.R. Dolbier Jr., S. Ait-Mohand, and M. Médebielle Tetrahedron Lett. 42 2001 3459
7. M. Médebielle, R. Keirouz, E. Okada, and T. Ashida Synlett 6 2001 821
8. M. Médebielle, O. Onomura, R. Keirouz, E. Okada, H. Yano, and T. Terauchi Synthesis 2002 2601
9. E. Okada, Y. Otsuki, M. Shinohara, M. Médebielle, Y. Shimizu, and H. Takeuchi Tetrahedron Lett. 44 2003 741
10. J.T. Welch, and S. Eswarakrishnan Fluorine in Bioorganic Chemistry 1991 Wiley New York, USA
11. C. Burkholder, W.R. Dolbier Jr., and M. Médebielle J. Org. Chem. 63 1998 5385
12. C. Burkholder, W.R. Dolbier Jr., and M. Médebielle J. Fluorine Chem. 102 2000 369
13. W.J. Middleton J. Org. Chem. 40 1975 574
14. R. Anilkumar, and D.J. Burton ArCHFCF2X (X = F, CI) derivatives have been recently synthesized by the fluorination of the corresponding alcohols with DAST, These intermediates were used for the synthesis of α, β,β-trifluorostyrenes Tetrahedron Lett. 44 2003 6661
15. R.P. Singh, B. Twamley, and J.M. Shreeve [RCF2CHF]2O derivatives were previously prepared via nucleophilic fluorination of glyoxal hydrates with Deoxofluor [(MeOCH2CH2)2-NSF3] J. Org. Chem. 67 20021918
16. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
17. H. Fukuda, and T. Kitazume J. Fluorine Chem. 74 1995 171
18. H. Eto, Y. Kaneko, and T. Sakamoto Chem. Pharm. Bull. 48 2000 982
19. P.A. Messina, K.C. Mange, and W.J. Middleton J. Fluorine Chem. 42 1989 137
20. M.E. Christy, C.D. Colton, M. Mackay, W.H. Staas, J.B. Wong, E.L. Engelhardt, M. Torchiana, and C.A. Stone J. Med. Chem. 3 1977 421
21. P. Kirsch, F. Huber, M. Lenges, and A. Taugerbeck Tetrafluoroethane derivatives are important intermediates for the elaboration of fluorinated liquid crystals J. Fluorine Chem. 112 2001 69
22. M.J. Robins, J.S. Wilson, and F. Hansske J. Am. Chem. Soc. 105 1985 4059
23. Y. Ding, J. Wang, K.A. Abboud, Y. Xu, W.R. Dolbier Jr., and N.G.J. Richards J. Org. Chem. 66 2001 6381
24. C. Moog, A. Wick, P. Le Ber, A. Kim, and A.M. Aubertin Antiviral. Res. 24 1994 275
25. Work in progress with Pr. B. T. Fan and Dr. F. Barbault (Université Denis Diderot Paris 7, ITODYS, UMR CNRS 7086).
26. W.C. Still, and M. Kahn J. Org. Chem. 43 1978 2923