A convenient one-step synthesis of fluoroethylidene derivatives

Tetrahedron Letters

Volumn 44, Issue 44, 2003, Pages 8127-8130

  Chevrie, D ^a   Lequeux, T ^a   Demoute, J P ^b   Pazenok, S ^b  

^a UNIVERSITÉ DE CAEN   (France)

^b BAYER CROPSCIENCE AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 FLUOROETHYL)SULFONYL 1,3 BENZOTHIAZOLE; ALDEHYDE; ALKENE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; FLUORINATION; MEDICAL LITERATURE; ROOM TEMPERATURE; SYNTHESIS;

DRYAS IULIA;

EID: 0141545221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.027     Document Type: Article

References (35)

1. Demoute, J. P.; Adams, A.; Demassey, J.; Babin, D. Patent WO 9,932,426, 1999; Chem. Abstr. 1999, 131, 73815.
2. Burton D.J., Yang Z., Qiu W. Chem. Rev. 96:1996;1641-1715. and references cited therein.
3. Xu Z., Desmarteau D.D. J. Chem. Soc., Perkin Trans. 1. 1992;313-315.
4. Etemad-Moghadam G., Seyden-Penne J. Bull. Soc. Chim. Fr. 1985;448-454.
5. McCarthy J.R., Huber E.W., Le T., Laskovic M., Matthews D.P. Tetrahedron. 52:1996;45-58.
6. Veenstra S.J., Hauseer K., Felber P. Bioorg. Med. Chem. Lett. 7:1997;351-354.
7. Burton D.J., Greenlimb P.E. J. Org. Chem. 40:1975;2796-2801.
8. Blackburn G.M., Parratt M. J. Chem. Soc., Chem. Commun. 1983;886-888.
9. McCarthy J.R., Matthews D.P., Edwards M.L., Stemerick D.M., Jarvi E.T. Tetrahedron Lett. 31:1990;5449-5452.
10. Moore W.R., Schatzman G.L., Jarvi E.T., Gross R.S., McCarthy J.R. J. Am. Chem. Soc. 114:1992;360-361.
11. Satoh T., Itoh N., Onda K., Kitoh Y., Yamakawa K. Tetrahedron Lett. 33:1992;1483-1484.
12. McCarthy J.R., Matthews D.P., Stemerick D.M., Huber E.W., Bey P., Lippert B.J., Snyder R.D., Sunkara P.S. J. Am. Chem. Soc. 113:1991;7439-7440.
13. Welch J.T., Lin J. Tetrahedron. 52:1996;291-304.
14. Yoshida M., Hara S., Fukuhara T., Yoneda N. Tetrahedron Lett. 41:2000;3887-3890.
15. Chen C., Wilcoxen K., Strack N., McCarthy J.R. Tetrahedron Lett. 40:1999;827-830.
16. Allmendinger T., Furet P., Hungerbûhler E. Tetrahedron Lett. 31:1990;7297-7300.
17. Baudin J.B., Hareau G., Julia S.A., Lorne R., Ruel O. Bull. Soc. Chim. Fr. 130:1993;856-878.
18. Baudin J.B., Hareau G., Julia S.A., Ruel O. Tetrahedron Lett. 32:1991;1175-1178.
19. Baudin J.B., Hareau G., Julia S.A., Ruel O. Bull. Soc. Chim. Fr. 130:1993;336-357.
20. For example see: (a) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285-296; (b) Smith, N. D.; Kocienski, P.; Street, S. D. Synthesis 1996, 652-666; (c) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681-694; (d) Charrette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328; (e) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
21. For example see: (a) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285-296; (b) Smith, N. D.; Kocienski, P.; Street, S. D. Synthesis 1996, 652-666; (c) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681-694; (d) Charrette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328; (e) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
22. For example see: (a) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285-296; (b) Smith, N. D.; Kocienski, P.; Street, S. D. Synthesis 1996, 652-666; (c) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681-694; (d) Charrette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328; (e) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
23. For example see: (a) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285-296; (b) Smith, N. D.; Kocienski, P.; Street, S. D. Synthesis 1996, 652-666; (c) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681-694; (d) Charrette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328; (e) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
24. For example see: (a) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285-296; (b) Smith, N. D.; Kocienski, P.; Street, S. D. Synthesis 1996, 652-666; (c) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681-694; (d) Charrette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328; (e) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
25. Demoute, J. P.; Hömberger, G.; Pazenok, S.; Babin, D. Patent WO 0,134,592, 2001; Chem. Abstr. 2001, 134, 366801.
26. Goralski C.T., Burk G.A. J. Org. Chem. 42:1977;3094-3096.
27. Lal G.S. J. Org. Chem. 58:1993;2791-2796.
28. Taylor S.D., Kotoris C.C., Hum G. Tetrahedron. 55:1999;12431-12477.
29. Franz R. J. Fluorine Chem. 15:1980;423-434.
30. Jouen C., Lemaître S., Lequeux T., Pommelet J.-C. Tetrahedron. 54:1998;10801-10810.
31. Lequeux T., Lebouc F., Lopin C., Yang H., Gouhier G., Piettre S. Org. Lett. 3:2001;185-188.
32. Gouault S., Pommelet J.C., Lequeux T. Synlett. 2002;996-998.
33. +): 244.998. Found: 245.005.
34. +): 186.106. Found: 186.099.
35. Pazenok, S.; Demoute, J. P.; Zard, S.; Lequeux, T. Patent WO 0,240,459, 2002; Chem. Abstr. 2002, 136, 386131.