Catalytic trifluoromethylation of uracil to 5-trifluoromethyluracil by use of CF3I and its industrial applications

Applied Catalysis A: General

Volumn 342, Issue 1-2, 2008, Pages 137-143

  Uraguchi, Daisuke ^a   Yamamoto, Kyoko ^a   Ohtsuka, Yuhki ^a   Tokuhisa, Kenji ^b   Yamakawa, Tetsu ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOSOH CORPORATION   (Japan)

Author keywords

5 Trifluoromethyluracil; Fe(II) catalyst; Trifluoromethyl iodide; Trifluoromethylation

Indexed keywords

CATALYST ACTIVITY; DERIVATIVES; INDUSTRIAL APPLICATIONS; IRON COMPOUNDS; OXIDATION;

TRIFLUOROMETHYL IODIDE; TRIFLUOROMETHYLATION;

ORGANIC COMPOUNDS;

EID: 43049162633     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2008.03.009     Document Type: Article

References (37)

1. The term of "5-trifluoromethyluracil" should be "5-trifluoromethylpyridine-2,4(1H,3H)-dion followed by the nomenclature of IUPAC. Expediently, we named the products obtained here as the substituted uracils. The systematic names of g and l are mentioned in 4. 5.
2. Dolman N.P., More J.C.A., Alt A., Knauss J.L., Pentikäinen O.T., Glasser C.R., Bleakman D., Mayer M.L., Collingridge G.L., and Jane D.E. J. Med. Chem. 50 (2007) 1558-1570
3. Salvetti R., Marchand A., Pregnolato M., Verri A., Spadari S., Focher F., Briant M., Sommadossi J.-P., Mathe C., and Gosselin G. Bioorg. Med. Chem. 9 (2001) 1731-1738
4. Iltzsch M.H., and Tankersley K.O. Biochem. Pharmacol. 48 (1994) 781-791
5. Iltzsch M.H., and Klenk E.E. Biochem. Pharm. 46 (1993) 1849-1858
6. Wigdahl B.L., Parkhurst J.R., and Rodney J. Antimicrob. Agents Chemother. 14 (1978) 470-475
7. Fuchikami T., and Ojima I. Tetrahedron Lett. 23 (1982) 4099-4100
8. Fuchikami T., Yamanouchi A., and Ojima I. Synthesis (1984) 766-768
9. Andres P., and Marhold A. J. Fluorine Chem. 77 (1996) 93-95
10. Kobayashi Y., Yamamoto K., Asai T., Nakano M., and Kumadaki I. J. Chem. Soc., Perkin Trans. I (1980) 2755-2761
11. Mertes M.P., and Saheb S.E. J. Pharm. Sci. 52 (1963) 508-509
12. Chambers R.D. Fluorine in Organic Chemistry (2004), Blackwell Publishing Ltd., Oxford
13. Lin J.-H., LeBreton P.R., and Shipman L.L. J. Phys. Chem. 84 (1980) 431-435
14. The net charges calculated with B3LYP/6-31+G** using Gaussian 03 Revision D.02 (Gaussian Inc., Wallingford CT 2004) were -0.394 at the 5-position and +0.033 at the 6-position.
15. Umemoto T., and Ishihara S. Tetrahedron Lett. 31 (1990) 3579-3582
16. Tanabe Y., Matsuo N., and Ohno N. J. Org. Chem. 53 (1988) 4582-4585
17. Schwarz B., Cech D., and Reefschlager J. J. Prakt. Chem. 326 (1984) 985-993
18. Hein L., and Cech D. Z. Chem. 11 (1977) 415-416
19. Akiyama T., Kato K., Kitajima M., Sakaguchi Y., Nakamura J., Hayashi H., and Sugimori A. Bull. Chem. Soc. Jpn. 61 (1988) 3531-3537
20. Dolbier Jr. W.R. Chem. Rev. 96 (1996) 1557-1584
21. Itoh Y., and Mikami K. Org. Lett. 7 (2005) 4883-4885
22. Yajima T., Nagano H., and Saito C. Tetrahedron Lett. 44 (2003) 7027-7029
23. Brace N.O. J. Fluorine Chem. 96 (1999) 101-127
24. 2O, methanol and ethanol are 220 mg, 83 mg and 41 mg.
25. Minisci F., Vismara E., and Fontana F. J. Org. Chem. 54 (1989) 5224-5227
26. Bravo A., Bjørsvik H.-R., Fontana F., Liguori L., Mele A., and Minisci F. J. Org. Chem. 62 (1997) 7128-7136
27. Baciocchi E., and Muraglia E. Tetrahedron Lett. 34 (1993) 3799-3800
28. Baciocchi E., and Muraglia E. Tetrahedron Lett. 34 (1993) 5015-5018
29. Dorfman L.M., and Adams G.E. Reactivity of the Hydroxyl Radical in Aqueous Solutions, NSRDS-NBS-46 (1973), U.S. Government Printing Office, Washington
30. Goldstein S., Meyerstein D., and Czapski G. Free Radic. Biol. Med. 153 (1993) 435-445
31. Sawyer D.T., Sobkowski A., and Matsushita T. Acc. Chem. Res. 29 (1996) 409-416
32. Tosoh, Inc., Sagami Chemical Research Center, JP 2007-74953.
33. De Pasquale R.J. Ind. Eng. Chem. Prod. Res. Dev. 17 (1978) 278-286
34. Mitsu Toatsu Chemicals, Inc., EP 0 635 517 and references therein.
35. Connely N.G., and Geiger W.E. Chem. Rev. 96 (1996) 877-910
36. Kong Y.-T., Imabayashi S., Kano K., Ikeda T., and Kakiuchi T. Am. J. Enol. Vitic. 52 (2001) 381-385
37. Khanna I.K., Weier R.M., Yu Y., Collins P.W., Miyashiro J.M., Koboldt C.M., Veenhuizen A.W., Currie J.L., Seibert K., and Isakson P.C. J. Med. Chem. 40 (1997) 1619-1633