Trifluoromethoxy substituted anilines: Metalation as the key step for structural elaboration

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4693-4699

  Leroux, Frédéric ^a   Castagnetti, Eva ^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

[No Author keywords available]

Indexed keywords

CARBOXYLATION; HYDROGEN; ISOMERS; LITHIUM; SYNTHESIS (CHEMICAL);

METALATION;

ORGANIC COMPOUNDS;

1,4 DIHYDRO 6 TRIFLUOROMETHOXY 2H 3,1 BENZOXAZIN 2 ONE; 2 [(TERT BUTOXYCARBONYL)AMINO] 3 (TRIFLUOROMETHOXY)BENZOIC ACID; 2 [(TERT BUTYLOXYCARBONYL)AMINO] 5 (TRIFLUOROMETHOXY)BENZOIC ACID; 2 AMINO 3 (TRIFLUOROMETHOXY)BENZOIC ACID; 2 AMINO 5 (TRIFLUOROMETHOXY)BENZOIC ACID; 2 AMINO 6 (TRIFLUOROMETHOXY)BENZOIC ACID; 3 TRIFLUOROMETHOXY N (TRIMETHYLSILYL)ANILINE; 3 TRIFLUOROMETHOXY N,N BIS(TRIMETHYLSILYL)ANILINE; 4 AMINO 2 (TRIFLUOROMETHOXY)BENZOIC ACID; 5 (2 FLUOROPHENYL) 1,3 DIHYDRO 7 TRIFLUOROMETHOXY 2H 1,4 BENZODIAZEPIN 2 ONE; 5 AMINO 2 (TRIFLUOROMETHOXY)BENZOIC ACID; 7 CHLORO 1,3 DIHYDRO 3 HYDROXY 5 [2 (TRIFLUOROMETHOXY)PHENYL] 2H 1,4 BENZODIAZEPIN 2 ONE; ANILINE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; LITHIUM DERIVATIVE; N TERT BUTOXYCARBONYL 2 (TRIFLUOROMETHOXY)ANILINE; N TERT BUTOXYCARBONYL 4 (TRIFLUOROMETHOXY)ANILINE; ORGANOMETALLIC COMPOUND; SEC BUTYLLITHIUM; TERT BUTYL N [2 (HYDROXYETHYL) 4 (TRIFLUOROMETHOXY)PHENYL]CARBAMATE; TERT BUTYL N [2 FORMYL 4 (TRIFLUOROMETHOXY)PHENYL]CARBAMATE; TERT BUTYL N [2 METHYL 3 (TRIFLUOROMETHOXY)PHENYL]CARBAMATE; TERT BUTYLLITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; CHEMICAL STRUCTURE; ISOMER; PROTON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037941265     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0267798     Document Type: Article

References (26)

1. Yagupolskii, L. M.; Yagupolskaya, L. N. Dokl. Akad. Nauk SSSR 1960, 134, 1381-1383; Chem. Abstr. 1961, 55, 55352i.
2. Yagupolskii, L. M.; Yagupolskaya, L. N. Dokl. Akad. Nauk SSSR 1960, 134, 1381-1383; Chem. Abstr. 1961, 55, 55352i.
3. Sheppard, W. A. J. Am. Chem. Soc. 1961, 83, 4860-4861.
4. Sheppard, W. A. J. Am. Chem. Soc. 1963, 85, 1314-1318.
5. Yagupolskii, L. M.; Bystrov, V. F.; Stepanyants, A. U.; Fialkov, Y. A. Zh. Obshch. Khim. 1964, 34, 3682-3690; Chem. Abstr. 1965, 62, 5175a.
6. Yagupolskii, L. M.; Bystrov, V. F.; Stepanyants, A. U.; Fialkov, Y. A. Zh. Obshch. Khim. 1964, 34, 3682-3690; Chem. Abstr. 1965, 62, 5175a.
7. Kuroboshi, M.; Kanie, K.; Hiyama, T. Adv. Synth. Catal. 2001, 343, 235-250.
8. Castagnetti, E.; Schlosser, M. Eur. J. Org. Chem. 2001, 691-695.
9. Schlosser, M.; Castagnetti, E. Eur. J. Org. Chem. 2001, 3991-3997.
10. Castagnetti, E.; Schlosser, M. Chem. Eur. J. 2002, 8, 799-804.
11. Schlosser, M. Eur. J. Org. Chem. 2001, 3975-3984.
12. Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4798-4801.
13. Cho, I.-s.; Gong, L.-y.; Muchowski, J. M. J. Org. Chem. 1991, 56, 7288-7291.
14. Takagishi, S.; Katsoulos., G.; Schlosser, M. Synlett 1992, 360-362.
15. Lamas, C.; Castedo, L.; Dominguez, D. Tetrahedron Lett. 1988, 29, 3865-3868.
16. Baston, E.; Maggi, R.; Friedrich, K.; Schlosser, M. Eur. J. Org. Chem. 2001, 3985-3989.
17. Mongin, F.; Maggi, R.; Schlosser, M. Chimia 1996, 50, 650-652.
18. Schlosser, M. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Wiley: Chichester, UK, 2002; pp 1-352, spec. 253-259.
19. Gschwend, H. W.; Hamdan, A. J. Org. Chem. 1982, 47, 3652-3657.
20. Meyers, A. I.; Lutomski, K. A. Synthesis 1983, 105-107.
21. Sternbach, L. H.; Reeder, E.; Keller, O.; Metlesics, W. J. Org. Chem. 1961, 26, 4488-4497.
22. Sternbach, L. H.; Fryer, R. I.; Metlesics, W.; Reeder, E.; Sach, G.; Saucy, G.; Stempel, A. J. Org. Chem. 1962, 27, 3788-3796.
23. Sternbach, L. H. J. Med. Chem. 1979, 22, 1-7.
24. Wang, Q.; Wei, H.-x.; Schlosser, M. Eur. J. Org. Chem. 1999, 3263-3268.
25. Bobbio, C.; Schlosser, M. Eur. J. Org. Chem. 2001, 4533-4536.
26. Frank, K. E.; Aube, J. J. Org. Chem. 2000, 65, 655-666.