Chemoselectivity in the reactions between ethyl 4,4,4-trifluoro-3-oxobutanoate and anilines: Improved synthesis of 2-trifluoromethyl-4- and 4-trifluoromethyl-2-quinolinones

Synthesis

Volumn , Issue 13, 2003, Pages 2005-2010

  Berbasov, Dmitrii O ^a   Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Chemoselectivity; Enamino esters; Fluorine; Keto amides; Quinolines

Indexed keywords

AMINES; POWDER METALS; REACTION KINETICS; WATER;

NEAR-CRITICAL WATER;

SYNTHESIS (CHEMICAL);

ALKYL GROUP; ANILINE DERIVATIVE; ETHYL 4,4,4 TRIFLUORO 3 OXOBUTANOATE; QUINOLONE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE;

EID: 0141506889     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41043     Document Type: Article

References (19)

1. Marull, M.; Schlosser, M. Eur. J. Org. Chem 2003, 1576; and references cited therein.
2. Lefebvre, O.; Marull, M.; Schlosser, M. Eur. J. Org. Chem. 2003, 2115; and references cited therein.
3. Schlosser, M.; Marull, M. Eur. J. Org. Chem. 2003, 1569.
4. Cottet, F.; Marull, M.; Lefebvre, O.; Schlosser, M. Eur. J. Org. Chem. 2003, 1559.
5. Soloshonik, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030.
6. Soloshonik, V. A.; Ono, T.; Soloshonik, I. V. J. Org. Chem. 1997, 62, 7538.
7. Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1997, 53, 8307.
8. Soloshonok, V. A.; Ohkura, H.; Uneyama, K. Tetrahedron Lett. 2002, 43, 5449.
9. Ohkura, H.; Berbasov, D. O.; Soloshonok, V. A. Tetrahedron 2003, in press.
10. 2)the starting keto ester 3 and anilines 4 were used in a ratio of 2:1; accordingly, the corresponding yields of the products 2 are calculated based on 4. Despite the fact that keto ester 3 is a cheap technical bulkware, it is still more expensive than most of the anilines 4, therefore, we believe that the chemical yields, as one of the criteria of synthetic efficiency, should be calculated on 3 to make an economical sense.
11. Kobayashi, Y.; Kumadaki, I.; Taguchi, S. Chem. Pharm. Bull. 1969, 17, 2335.
12. Liu, J.; LU, H. J. J. Fluorine Chem. 2001, 111, 207.
13. For additional references on the synthesis of trifluoromethyl-containing compounds of type 5 and 6, see the following papers suggested by a referee: (a) Latham, E. J.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1 1997, 2059. (b) Combs, D. W.; Reed, M. S.; Klaubert, D. H. Synth. Commun. 1992, 22, 323. (c) Bajwa, G. S.; Joullie, M. M. J. Heterocycl. Chem. 1972, 9, 1403. (d) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramires de Arrellano, M. C.; Fuentes, A. S. J. Org. Chem 2002, 67, 4667. (e) Stanforth, S. P. Tetrahedron 2002, 57, 1833.
14. For additional references on the synthesis of trifluoromethyl-containing compounds of type 5 and 6, see the following papers suggested by a referee: (a) Latham, E. J.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1 1997, 2059. (b) Combs, D. W.; Reed, M. S.; Klaubert, D. H. Synth. Commun. 1992, 22, 323. (c) Bajwa, G. S.; Joullie, M. M. J. Heterocycl. Chem. 1972, 9, 1403. (d) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramires de Arrellano, M. C.; Fuentes, A. S. J. Org. Chem 2002, 67, 4667. (e) Stanforth, S. P. Tetrahedron 2002, 57, 1833.
15. For additional references on the synthesis of trifluoromethyl-containing compounds of type 5 and 6, see the following papers suggested by a referee: (a) Latham, E. J.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1 1997, 2059. (b) Combs, D. W.; Reed, M. S.; Klaubert, D. H. Synth. Commun. 1992, 22, 323. (c) Bajwa, G. S.; Joullie, M. M. J. Heterocycl. Chem. 1972, 9, 1403. (d) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramires de Arrellano, M. C.; Fuentes, A. S. J. Org. Chem 2002, 67, 4667. (e) Stanforth, S. P. Tetrahedron 2002, 57, 1833.
16. For additional references on the synthesis of trifluoromethyl-containing compounds of type 5 and 6, see the following papers suggested by a referee: (a) Latham, E. J.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1 1997, 2059. (b) Combs, D. W.; Reed, M. S.; Klaubert, D. H. Synth. Commun. 1992, 22, 323. (c) Bajwa, G. S.; Joullie, M. M. J. Heterocycl. Chem. 1972, 9, 1403. (d) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramires de Arrellano, M. C.; Fuentes, A. S. J. Org. Chem 2002, 67, 4667. (e) Stanforth, S. P. Tetrahedron 2002, 57, 1833.
17. For additional references on the synthesis of trifluoromethyl-containing compounds of type 5 and 6, see the following papers suggested by a referee: (a) Latham, E. J.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1 1997, 2059. (b) Combs, D. W.; Reed, M. S.; Klaubert, D. H. Synth. Commun. 1992, 22, 323. (c) Bajwa, G. S.; Joullie, M. M. J. Heterocycl. Chem. 1972, 9, 1403. (d) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramires de Arrellano, M. C.; Fuentes, A. S. J. Org. Chem 2002, 67, 4667. (e) Stanforth, S. P. Tetrahedron 2002, 57, 1833.
18. (a) Gildemeister, H.; Knorr, H.; Mildenberger, H.; Salbeck, G. Liebigs Ann. Chem. 1982, 1656.
19. (b) Staskun, B.; Israelstam, S. S. J. Org. chem. 1961, 26, 3191.