The direct metalation and subsequent functionalization of trifluoromethyl-substituted pyridines and quinolines

European Journal of Organic Chemistry

Volumn , Issue 8, 2003, Pages 1569-1575

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

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

^b Institut de Mathématiques B   (Switzerland)

Author keywords

Carboxylation; Caub re's base; Dialkylamides; Fluorinated building blocks; Heterocycles; Lithium; Optional site selectivity; Regioisomers

Indexed keywords

2 (TRIFLUOROMETHYL)PYRIDINE; 2 (TRIFLUOROMETHYL)QUINOLINE; 2 TRIFLUOROMETHYL 3 PYRIDINECARBOXYLIC ACID; 2 TRIFLUOROMETHYL 3 QUINOLINECARBOXYLIC ACID; 2 TRIFLUOROMETHYL 8 QUINOLINECARBOXYLIC ACID; 3 (TRIFLUOROMETHYL)PYRIDINE; 3 (TRIFLUOROMETHYL)QUINOLINE; 3 TRIFLUOROMETHYL 2 QUINOLINECARBOXYLIC ACID; 3 TRIFLUOROMETHYL 4 QUINOLINECARBOXYLIC ACID; 4 (TRIFLUOROMETHYL)PYRIDINE; 4 (TRIFLUOROMETHYL)QUINOLINE; 4 TRIFLUOROMETHYL 2 PYRIDINECARBOXYLIC ACID; 4 TRIFLUOROMETHYL 2 QUINOLINECARBOXYLIC ACID; 4 TRIFLUOROMETHYL 3 PYRIDINECARBOXYLIC ACID; 4 TRIFLUOROMETHYL 3 QUINOLINECARBOXYLIC ACID; 6 TRIFLUOROMETHYL 2 PYRIDINECARBOXYLIC ACID; BASE; CARBOXYLIC ACID DERIVATIVE; LITHIUM DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBOXYLATION; CHEMICAL MODIFICATION; DECOMPOSITION; DEPROTONATION; ISOMER; METALATION; STEREOCHEMISTRY;

EID: 0037884973     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390216     Document Type: Article

References (36)

1. H. H. Büker, N. M. M. Nibbering, D. Espinosa, F. Mongin, M. Schlosser, Tetrahedron Lett. 1997, 38, 8519-8522.
2. M. Schlosser, F. Mongin, J. Porwisiak, W. Dmowski, H. H. Büker, N. M. M. Nibbering, Chem. Eur. J. 1998, 4, 1281-1286.
3. M. Schlosser, E. Marzi, F. Cottet, H. H. Büker, N. M. M. Nibbering, Chem. Eur. J. 2001, 7, 3511-3516.
4. J. D. Roberts, D. Y. Curtin, J. Am. Chem. Soc. 1946, 68, 1658-1660.
5. M. Schlosser, G. Katsoulos, S. Takagishi, Synlett 1990, 747-748.
6. M. Schlosser, Eur. J. Org. Chem. 2001, 3975-3984.
7. M. Schlosser, in, Organometallics in Synthesis: A Manual (Ed.: M. Schlosser), 2nd ed., Wiley, Chichester, 2002, pp. 1-352, spec. 253-257.
8. P. Gros, Y. Fort, G. Quéguiner, P. Caubère, Tetrahedron Lett. 1995, 36, 4791-4794.
9. P. Gros, Y. Fort, P. Caubère, J. Chem. Soc., Perkin Trans. 1 1998, 1685-1689.
10. I. F. Tupitsyn, N. N. Zatsepina, A. V. Kirova, Y. L. Kaminskii, A. G. Ivanenko, Reakts. Sposobnost Org. Soedin. 1973, 10, 143-162; Chem. Abstr. 1973, 79, 114928v.
11. I. F. Tupitsyn, N. N. Zatsepina, A. V. Kirova, Y. L. Kaminskii, A. G. Ivanenko, Reakts. Sposobnost Org. Soedin. 1973, 10, 143-162; Chem. Abstr. 1973, 79, 114928v.
12. O. A. Reutov, I. P. Beletskaya, K. P. Butin, CH-Acids, Pergamon Press, Oxford, 1978, pp. 111-114.
13. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, Butterworth, London, 1965.
14. J. Porwisiak, W. Dmowski, Tetrahedron 1994, 50, 12259-12266.
15. F. Cottet, M. Marull, O. Lefebvre, M. Schlosser, Eur. J. Org. Chem. 2003, 1559-1568, preceding article.
16. A. E. Tschitschibabin, Ber. Dtsch. Chem. Ges. 1907, 40, 1810 -1819.
17. K. Ziegler, H. Zeiser, Justus Liebigs Ann. Chem. 1931, 485, 174-192.
18. J. C. W. Evans, C. P. H. Allen, Org. Synth., Coll. Vol. 1943, 2, 517-518.
19. W. Dmowski, J. Porwisiak, J. Fluorine Chem. 1992, 59, 321-331.
20. A. A. Kolomeitsev, V. N. Movchun, Y. L. Yagupolskii, J. Porwisiak, W. Dmowski, Tetrahedron Lett. 1992, 33, 6191-6192.
21. H. Koroniak, P. Fiedorow, W. Dmowski, J. Porwisiak, J. Mol. Struct. 1995, 351, 187-195.
22. I. F. Tupitsyn, N. N. Zatsepina, A. V. Kirova, Y. M. Kapustin, Org. React. 1968, 5, 601- 612; Chem. Abstr. 1969, 70, 76940x.
23. I. F. Tupitsyn, N. N. Zatsepina, A. V. Kirova, Y. M. Kapustin, Org. React. 1968, 5, 601- 612; Chem. Abstr. 1969, 70, 76940x.
24. J. A. Zoltewicz, A. A. Sale, J. Am. Chem. Soc. 1973, 95, 3928-3931.
25. M. S. Raasch, J. Org. Chem. 1962, 27, 1406-1409.
26. A. S. Dey, M. M. Joullié, J. Heterocycl. Chem. Chem. 1965, 2, 113-119.
27. F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330.
28. Y. Kobayashi, I. Kumadaki, S. Taguchi, Chem. Pharm. Bull. 1969, 17, 2335-2339.
29. Y. Kobayashi, I. Kumadaki, S. Sato, N. Hara, E. Chikami, Chem. Pharm. Bull. 1970, 18, 2334-2339.
30. Y. Kobayashi, I. Kumadaki, A. Ohsawa, T. Yamada, Chem. Pharm. Bull. 1972, 20, 1839-1839.
31. J. M. Paratian, S. Sibille, J. Perichon, J. Chem. Soc., Chem. Commun. 1992, 53-54.
32. H. Keller, M. Schlosser, Tetrahedron 1996, 52, 4637-4644.
33. M. Marull, M. Schlosser, Eur. J. Org. Chem. 2003, 1576-1588, following article.
34. O. Lefebvre, M. Marull, M. Schlosser, manuscript in preparation [title: 4-(Trifluoromethyl)quinoline Derivatives].
35. K. Ziegler, F. Crössmann, H. Kleinert, O. Schäfer, Justus Liebigs Ann. Chem. 1929, 473, 1-35, spec. 20.
36. H. Metzger, E. Müller, in Houben-Weyl: Methoden der organischen Chemie (Ed.: E. Müller), Thieme, Stuttgart, 1959, Vol. 1/2, pp. 321-384, spec. 337-338.