Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones

European Journal of Organic Chemistry

Volumn , Issue 8, 2003, Pages 1576-1588

  Marull, Marc ^a   Schlosser, Manfred ^a,b  

^a Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Bromine lithium exchange; Ethyl 4,4,4 trifluoroacetoacetate; Heterocycles; Hydrogen lithium exchange; Regioselectivity

Indexed keywords

1,4 DIHYDRO 2 TRIFLUOROMETHYL 4H 4 QUINOLINONE; 2 (TRIFLUOROMETHYL)QUINOLINONE DERIVATIVE; 2 TRIFLUOROMETHYL 4 QUINOLYLLITHIUM; 4 BROMO 2 (TRIFLUOROMETHYL)QUINOLINE; 4 BROMO 2 TRIFLUOROMETHYL 3 QUINOLYLLITHIUM; 4,4,4 TRIFLUOROACETOACETATE; ACID; ANILINE DERIVATIVE; BUTYLLITHIUM; LITHIUM DIISOPROPYLAMIDE; ORGANOLITHIUM COMPOUND; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMOREACTIVITY; CYCLIZATION; HALOGEN METAL EXCHANGE; HYDROGEN METAL EXCHANGE; POLYMERIZATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0038708560     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390217     Document Type: Article

References (43)

1. Brit. Pat. GB 931 689 (Farbwerke Hoechst; priority: DE 19601217); Chem. Abstr. 1964, 60, 2788 g.
2. J.-P. Bégué, D. Bonnet-Delpon, R. Dogbeavou, M. Ourévitch, J. Chem. Soc., Perkin Trans. 1 1993, 2787-2791.
3. K. Kawada, O. Kitagawa, T. Taguchi, Y. Hanzawa, Y. Kobayashi, Y. Iitaka, Chem. Pharm. Bull. 1985, 33, 4216-4222.
4. H. Molines, C. Wakselman, J. Chem. Soc., Perkin Trans. 1 1980, 1114-1117.
5. J.-P. Bégué, D. Bonnet-Delpon, A. Dogbeavou, Synth. Commun. 1992, 22, 573-579.
6. E. R. Bissell, A. R. Mitchell, R. E. Smith, J. Org. Chem. 1980, 45, 2283-2287.
7. H. Ogoshi, M. Homma, K. Yokota, H. Toi, Y. Aoyama, Tetrahedron Lett. 1983, 24, 929-930.
8. R. A. Jones, D. C. Rustidge, S. M. Cushman, Synth. Commun. 1984, 14, 575-584.
9. P. Bravo, D. Dillido, G. Resnati, Tetrahedron 1994, 50, 8827-8836.
10. P. J. Sanfilippo, M. C. Jetter, R. Cordovy, R. A. Noe, E. Chourmouzis, C. Y. Lau, E. Wang, J. Med. Chem. 1995, 38, 1057-1059.
11. G. F. Grillot, S. Aftergut, D. G. Botteron, J. Org. Chem. 1958, 23, 119-6297.
12. G. de Stevens, A. Halamandaris, P. Wenk, L. Dorfman, J. Am. Chem. Soc. 1959, 81, 6292-6297.
13. K. H. Pilgram, R. D. Skiles, J. Heterocycl. Chem. 1988, 25, 139-143.
14. L. F. Lee, F. M. Schleppnik, R. W. Schneider, D. H. Campbell, J. Heterocycl. Chem. 1990, 27, 243-245.
15. B. J. Gaede, L. L. McDermott, J. Heterocycl. Chem. 1993, 30, 49-54.
16. R. Balicki, P. Nantka-Namirski, Acta Pol. Pharm. 1974, 31, 261-263; Chem. Abstr. 1975, 82, 72739p.
17. R. Balicki, P. Nantka-Namirski, Acta Pol. Pharm. 1974, 31, 261-263; Chem. Abstr. 1975, 82, 72739p.
18. R. Balicki, Pol. J. Chem. 1984, 58, 97-102; Chem. Abstr. 1985, 103, 104908p.
19. R. Balicki, Pol. J. Chem. 1984, 58, 97-102; Chem. Abstr. 1985, 103, 104908p.
20. R. W. Lang, P. F. Wenk, Helv. Chim. Acta 1988, 71, 596-601.
21. P. L. Ferrarini, C. Mori, G. Primofiori, L. Calzolari, J. Heterocycl. Chem. 1990, 27, 881-886.
22. A. Kreutzberger, M. Sellheim, J. Fluorine Chem. 1985, 27, 203-212.
23. A. Kreutzberger, J. Gillessen, J. Fluorine Chem. 1985, 29, 387-397.
24. A. Kreutzberger, H. Schimmelpfennig, Arch. Pharm. (Weinheim) 1981, 314, 34-41; Chem. Abstr. 1981, 95, 97700.
25. A. Kreutzberger, H. Schimmelpfennig, Arch. Pharm. (Weinheim) 1981, 314, 34-41; Chem. Abstr. 1981, 95, 97700.
26. M. Angelo, D. Ortwine, D. Worth, L. M. Werbel, J. Med. Chem. 1983, 26, 1258-1267.
27. M. M. Angelo, D. Ortwine, D. Worth, L. M. Werbel, J. Med. Chem. 1982, 26, 1311-1316.
28. A. S. Dey, M. M. Joullié, J. Heterocycl. Chem. 1965, 2, 113-119.
29. R. M. Pinder, A. Burger, J. Med. Chem. 1968, 11, 267-169.
30. A. R. Patel, C. J. Ohnmacht, D. P. Clifford, A. S. Crosby, R. E. Lutz, J. Med. Chem. 1971, 14, 198-202.
31. C. J. Ohnmacht, A. R. Patel, R. E. Lutz, J. Med. Chem. 1971, 14, 926-928.
32. G. S. Bajwa, M. M. Joullié, J. Heterocycl. Chem. 1972, 9, 1403-1405.
33. D. L. Nguyên, M. Schlosser, Helv. Chim. Acta 1977, 60, 2085-2088.
34. R. Adams, H. C. Yuan, Chem. Rev. 1933, 12, 261-338.
35. F. H. Westheimer, in Steric Effects in Organic Chemistry (Ed.: M. S. Newman), Wiley, New York, 1956, pp. 523-555, spec. 552-554.
36. F. Mongin, E. Marzi, M. Schlosser, Eur. J. Org. Chem. 2001, 2771-2777.
37. N. S. Narasimhan, N. M. Sunder, R. Ammanamanchi, B. D. Bonde, J. Am. Chem. Soc. 1990, 112, 4431-4435.
38. D. J. Gallagher, P. Beak, J. Am. Chem. Soc. 1991, 113, 7984-7987.
39. M. Schlosser, J. Porwisiak, F. Mongin, Tetrahedron 1998, 54, 895-900.
40. Q. Wang, H.-x. Wei, M. Schlosser, Eur. J. Org Chem. 1999, 3263-3268.
41. C. Bobbio, M. Schlosser, Eur. J. Org. Chem. 2001, 4533-4536.
42. H. Keller, M. Schlosser, Tetrahedron 1996, 52, 4637-4644.
43. D. G. Coe, S. R. Landauer, H. N. Rydon, J. Chem. Soc. 1954, 2281-2288.