New regiospecific synthesis of 2-trifluoromethyl-1,5 diazapentadiene compounds and of 2-trifluoromethylquinolines, their cyclization products

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8327-8331

  El Kharrat, Salem ^a   Skander, Myriem ^a   Dahmani, Abdelkader ^a   Laurent, Philippe ^a   Blancou, Hubert ^a  

^a UNIV MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; SYNTHESIS (CHEMICAL);

2-TRIFLUOROMETHYLQUINOLINES; ARYLAMINES; PERFLUOROALKYLATED GEMIODOACETOXY;

ORGANIC COMPOUNDS;

2 TRIFLUOROMETHYL 1,5 DIAZAPENTADIENE DERIVATIVE; 2 TRIFLUOROMETHYL DIAZAPENTADIENE DERIVATIVE; 2 TRIFLUOROMETHYLQUINOLINE DERIVATIVE; ALKYL GROUP; AROMATIC AMINE; GEMIODOACETOXY DERIVATIVE; IODINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; VINAMIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; RING CLOSING METATHESIS;

ANILINE COMPOUNDS; CYCLIZATION; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM; VINBLASTINE;

EID: 26844573778     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050586d     Document Type: Article

References (42)

1. Schofield, H. J. Fluorine Chem. 1999, 100, 7-11.
2. Gross, U.; Rüdiger, S. In Organo-Fluorine Compounds; Baasner, B., Hagemann, H., Tatlow, J. C., Eds.; Houben-Weyl Methods of Organic Chemistry; Thieme: Stuttgart, 1999; Vol. E10a, pp 18-26.
3. Elliott A. J. In Chemistry of Organic Fluorine Compounds II, A Critical Review; Hudlick M., Pavlath, A. E., Eds.; ACS Monograph 187, American Chemical Society: Washington, DC, 1995; pp 1119-1125.
4. Smart B. E. J. Fluorine Chem. 2001, 109, 3-11.
5. Ismail F. M. J. Fluorine Chem. 2002, 118, 27-33.
6. Kouznetsov, V. V.; Mendez, L. Y.; Gomez, C. M. Curr. Org. Chem. 2005, 9(2), 141-161.
7. (a) Chambers, R. D.; Holling, D.; Sandford, G.; Puschmann, H.; Howard, J. A. K. J. Fluorine Chem. 2002, 117, 99-101.
8. Chambers, R. D.; Holling, D.; Sandford, G.; Batsanov, A. S.; Howard, J. A. K. J. Fluorine Chem. 2004, 125, 661-671.
9. (b) Bonnet, V.; Mongin, F.; Trecourt, F.; Queguiner, G.; Knochel, P. Tetrahedron 2002, 58, 4429-4438.
10. Konig, W. Ber. 1923, 56, 1853.
11. Julia, M. Ann. Chim. (France) 1950, 595.
12. Gagan, J. M.; Lloyd, D. J. Chem. Soc., Chem. Commun. 1967, 1043.
13. Acheson, R. M.; Bolton, R. G. Tetrahedron Lett. 1973, 2827.
14. (a) Schroeder, G.; Luttke, W. Chem. Ber. 1972, 105, 2175.
15. (b) Palmer, M. H. J. Chem. Soc. 1962, 3645.
16. (a) McNab, H.; Murray, E. A. J. Chem. Soc., Perkin Trans, 1 1988, 333.
17. (b) McNab, H.; Murray, E. A. Arkivoc 2002, iii, 95.
18. Brace, N. O. J. Fluorine Chem. 1999, 93, 1-25.
19. Brace, N. O. U.S. Patent 3,145,222, August, 1964.
20. Krebs, A. Houben-Weyl. 1992, 14a/3, 85.
21. Schenk, W. K.; Kibitz, R.; Neuenschwander, M. Helv. Chem. Acta. 1975, 58, 1099.
22. March, J. Advanced Organic Chemistry, 3rd ed.; Wiley: New York, 1985; p 861.
23. Laurent, P.; Blancou, H.; Commeyras, A. Tetrahedron Lett. 1992, 2489.
24. Laurent, P.; Tra Ahn, D.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1999, 94, 139.
25. Brace, N. O. J. Org. Chem. 1962, 27, 3033.
26. Laurent, P.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1993, 62, 161.
27. Keller, H.; Schlosser, M. Tetrahedron 1996, 52, 4637.
28. Gagan, J. M. F.; Lloyd, D. J. Chem. Soc., Chem. Commun. 1967, 1043.
29. Lloyd, D. Gagan, J. M. F. J. Chem. Soc. C 1970, 2488.
30. Gagan, J. M. F.; Lloyd, D. J. Chem. Soc. C 1970, 2488.
31. Bradford, L.; Elliott, T. J.; Rowe, F. M. J. Chem. Soc. 1947, 437.
32. Palmer, M. H. J. Chem. Soc. 1962, 3645.
33. Wang, Q.-F.; Mao, Y.-Y.; Qin, C.-Y.; Zhu, S.-Z.; Hu, C.-M. Monatsh. Chem. 2000, 131, 55.
34. Dahmani, A.; Laurent, P.; Blancou, H. 16th International Symposium of Fluorine Chemistry, Durham, U.K., 2000.
35. El Kharrat, S.; Skander, M.; Laurent, P.; Blancou, H. 13th European Symposium on Fluorine Chemistry, Bordeaux, July 2001.
36. Richards, C. P.; Webb, G. A. Org. Magn. Reson. 1975, 7, 401.
37. Honeybourne, C. L.; Webb, G. A. Spectrochim. Acta A 1969, 25, 1075.
38. Lloyd, D.; McNab, H. Angew. Chem., Int. Ed. 1976, 15, 459.
39. Schlosser, M.; Keller, H.; Sumida, S-I.; Yang, J. Tetrahedron Lett. 1997, 49, 8523.
40. Acheson, R. M.; Bolton, R. G.; Tetrahedron Lett. 1973, 2821.
41. Schroeder, G.; Luttke, W. Chem. Ber. 1972, 105, 2175.
42. Jutz, J. C. Top. Curr. Chem. 1978, 73, 125-230.