Preparation of 10-Trifluoromethyl Artemether and Artesunate. Influence of Hexafluoropropan-2-ol on Substitution Reaction

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9763-9766

  Magueur, Guillaume ^a   Crousse, Benoit ^a   Ourévitch, Michèle ^a   Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SOLVENTS; SUBSTITUTION REACTIONS;

STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

10 TRIFLUOROMETHYL ARTEMETHER; 10 TRIFLUOROMETHYL BROMIDE; 10 TRIFLUOROMETHYL HEMIKETAL; ACETAL; ARTEMETHER; ARTESUNATE; BROMIDE; HEXAFLUORO 2 PROPANOL; HEXAFLUOROPROPAN 2 OL; METHANOL; METHYL CHLORIDE; PROPANE; PROPANOL; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0345529015     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035174o     Document Type: Article

References (31)

1. Klayman, D. L. Science 1985, 228, 1049-1055.
2. (a) Abouabdellah, A.; Bégué, J. P.; Bonnet-Delpon, D.; Gantier, J. C.; Thanh Nga, T. T.; Truong Dinh, T. Bioorg. Biomed. Chem. Lett. 1996, 2717-2720.
3. (b) Than Nga, T. T.; Ménage, C.; Bégué, J. P.; Bonnet-Delpon, D.; Gantier, J. C.; Pradines, B.; Doury, J. C.; T. D. Thac. J. Med. Chem. 1978, 21, 4101-4108.
4. Munier, P.; Giudicelli, M. B.; Picq, D.; Anker, D. J. Carbohydr. Chem. 1994, 13, 1225-1230.
5. (a) Allen, A. D.; Tidwell, T. T. In Advances in carbocation chemistry; Creary, X., Ed.; JAI Press Inc.: Greenwich, CT, 1989; pp 1-44.
6. (b) Creary, X. Chem. Rev. 1991, 91, 1625-1676.
7. (a) Matsutani, H.; Poras, H.; Kusumoto, T.; Hiyama, T. Synlett 1998, 1353-1354.
8. (b) Katagiri, T.; Minoru, I.; Uneyama, K. Tetrahedron: Asymmetry 1999, 10, 2583-2589.
9. (c) Hagiwara, T.; Tanaka, K.; Fuchikami, T. Tetrahedron Lett. 1996, 37, 8187-8190.
10. (a) Uneyama, K.; Momota, M.; Hayashida, K.; Itoh, T. J. Org. Chem. 1990, 55, 5364-5368.
11. (b) Nesi, M.; Brasca, M. G.; Longo, A.; Moretti, W.; Panzeri, A. Tetrahedron Lett. 1997, 4881-4884.
12. (c) Tongco, E. C.; Prakash, G. K. S.; Olah, G. A. Synlett 1997, 1193-1195.
13. (d) Kondratenko, M. A.; Malézieux, B.; Gruselle, M.; Bonnet-Delpon, D.; Bégué, J. P. J. Organomet. Chem. 1994, 487, C15-C17.
14. Chorki, F.; Grellepois, F.; Crousse, B.; Hoang, V. D.; Hung, N. V.; Bonnet-Delpon, D.; Bégué, J, P. Org. Lett. 2002, 4, 757-759.
15. Chorki, F.; Grellepois, F.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J. P. J. Org. Chem. 2001, 66, 7858-7863.
16. (a) Lin, A. J.; Lee, M.; Klayman, D. L. J. Med. Chem. 1989, 32, 1249-1252.
17. (b) Hindley, S.; Ward, S. E.; Storr, R. C.; Searle, N. L.; Bray, P. G.; Kevin Park, B.; Davies, J.; O'Neill, P. M. J. Med. Chem. 2002, 45, 1052-1063.
18. 2O, whereas no elimination was observed when hexane was used as solvent.
19. (a) Reichadt, C. Solvents and solvent effects in organic chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003.
20. (b) Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W J. Org. Chem. 1983, 48, 2877.
21. Haynes, R. K.; Chan, H. W.; Cheug, M. K.; Chung, S. T.; Lam, W. L.; Tsang, H. W.; Voerste, A.; Williams, I. D. Eur. J. Org. Chem. 2003, 2098-2114.
22. Bégué, J. P.; Benayoud, F.; Bonnet-Delpon, D. J. Org. Chem. 1995, 60, 5029-5036.
23. See, for example: (a) Allard, B.; Casadevall, A.; Casadevall, E.; Largeau, C. Nouv. J. Chim. 1980, 4, 539-545.
24. (b) Schadt, F. L.; Bentley, D. W.; Schleyer, P. V. R. J. Am. Chem. Soc. 1976, 98, 7667.
25. Iskra, J.; Bonnet-Delpon, D., Bégué, J. P. Eur. J. Org. Chem. 2002, 3402-3410.
26. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
27. Takita, R.; Oshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 4661-4665.
28. Grellepois, F.; Chorki, F.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J. P. J. Org. Chem. 2002, 67, 1253-1260.
29. (a) Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, 533-535.
30. (b) Heaney, H. Aldrichim. Acta 1993, 26, 35-45.
31. Legros, J.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J. P. Eur. J. Org. Chem 2002, 3290-3293.