Syntheses of 2-(trifluoromethyl)-1,3-dicarbonyl compounds through direct trifluoromethylation with CF 3I and their application to fluorinated pyrazoles syntheses

Tetrahedron

Volumn 68, Issue 12, 2012, Pages 2636-2649

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

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOSOH CORPORATION   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

2 (Trifluoromethyl) 1,3 dicarbonyl compounds; Cycloaddition; Fenton reagent; Fluorinated pyrazole; Trifluoromethylation

Indexed keywords

1,2 DICARBONYL DERIVATIVE; 1,3 DIKETONE; 2 (TRIFLUOROMETHYL) 1,3 DICARBONYL DERIVATIVE; AMIDE; CARBOXYLIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; FERROUS GLUCONATE; FLUORINE DERIVATIVE; HYDRAZINE DERIVATIVE; PYRAZOLE DERIVATIVE; TRIFLUOROIODOMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; METHYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; TRIFLUOROMETHYLATION;

EID: 84863407849     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.01.075     Document Type: Article

References (46)

1. J. Elguero, P. Goya, N. Jagerovic, and A.M.S. Silva Targets Heterocycl. Syst. 6 2002 52
2. C. Lamberth Heterocycles 71 2007 1467
3. J.-P. Bégué, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 Wiley Hoboken
4. J.C. Sloop, C.L. Bumgardner, and W.D. Loehle J. Fluorine Chem. 118 2002 135
5. V. Kumar, R. Aggarwal, and S.P. Singh Heterocycles 75 2008 2893
6. J.W. Lyga, and R.M. Patera J. Heterocycl. Chem. 27 1990 919
7. M.D. Threadgill, A.K. Heer, and B.G. Jones J. Fluorine Chem. 65 1993 21
8. A. Kimata, H. Nakagawa, R. Ohyama, T. Fukuuchi, S. Ohta, T. Suzuki, and N. Miyata J. Med. Chem. 50 2007 5053
9. L. Beverina, M. Crippa, M. Sassi, A. Monguzzi, F. Meinardi, R. Tubino, and G.A. Pagani Chem. Commun. 2009 5103
10. F. Gosselin, P.D. O'shea, R.A. Webster, R.A. Reamer, R.D. Tillyer, and E.J.J. Grabowski Synlett 2006 3267
11. A. Pace, S. Buscemi, and N. Vivona Org. Prep. Proced. Int. 37 2005 447
12. A.M. Gilbert, M.G. Bursavich, S. Lembardi, K.E. Georgiadis, E. Reifenberg, C.R. Flannery, and E.A. Morris Bioorg. Med. Chem. Lett. 17 2007 1189
13. D.C. England J. Org. Chem. 46 1981 147
14. T. Yokozawa, T. Nakai, and N. Ishikawa Tetrahedron Lett. 25 1984 3991
15. T. Iwaoka, T. Murohashi, N. Katagiri, M. Sato, and C. Kaneko J. Chem. Soc., Perkin Trans. 1 1992 1393
16. J.-C. Blazejewski, R. Dorme, and C. Wakselman Synthesis 1985 1120
17. Shreeve, J. M.; Yang, J.-J.; Kirchmeier, R. L. U.S. Patent 6,215,021.
18. K. Uneyama, and K. Ueda Chem. Lett. 1988 853
19. D. Uraguchi, K. Yamamoto, Y. Otsuka, T. Tokuhisa, and T. Yamakawa Appl. Catal., A 342 2008 137
20. T. Kino, Y. Nagase, D. Uraguchi, K. Yamamoto, Y. Otsuka, T. Tokuhisa, and T. Yamakawa J. Fluorine Chem. 131 2010 98
21. N.V. Belova, V.V. Sliznev, H. Oberhammer, and G. Girichev J. Mol. Struct. 978 2010 282
22. R.H. Wiley, and P.E. Hexner Organic Syntheses Collect. Vol. No. IV 1963 John Wiley & Sons New York, NY 351
23. J. Zheng, Z. Wang, and Y. Shen J. Fluorine Chem. 61 1993 17
24. Pelcman, B.; Sanin, A.; Nilsson, P.; Groth, T.; Kromann, H. WO 2007/051981
25. Y. Kobayashi, T. Yamashita, K. Takahashi, H. Kuroda, and I. Kumadaki Chem. Pharm. Bull. 32 1984 4402
26. H. Yamanaka, T. Takekawa, K. Morita, T. Ishikawa, and J.T. Gupton Tetrahedron Lett. 37 1996 1892
27. Hoffman, M. G.; Helmke, H.; Willms, L.; Auler, T.; Kehne, H.; Hills, M.; Feucht, D. WO2005/089551
28. Stetter, J.; Schallner, O.; Linding, M.; Jensen-Korte, U.; Baasner, B.; Becker, B.; Homeyer, B.; Behrenz, W.; Stendel, W. EP 0243636.
29. M. Guillaune, Z. Janousek, H.G. Viehe, C. Wynants, J.-P. Declercq, and B. Tinant J. Fluorine Chem. 69 1994 253
30. R. Bolton, C. Moore, and P.B. Candall J. Chem. Soc., Perkin Trans. 2 1982 1593
31. K. Burger, C. Zettl, F. Hein, and H. Schickaneder Chem. Ber. 112 1979 2620
32. Hirai, K.; Matsukawa, T.; Tokumura, J.; Kochi, S. WO1998/30547
33. S. Ikeda, Y. Kogame, and M. Okahara J. Org. Chem. 50 1985 3640
34. Y. Kamitori, M. Hojo, R. Masuda, S. Ohara, K. Kawasaki, and N. Yoshikawa Tetrahedron Lett. 29 1988 5281
35. Ueno, R.; Takabe, F.; Abe, T.; Izuki, Y.; Miyazaki, M.; Yamaji, M.; Kawasaki, H. JP 2000-219679.
36. M. Curini, O. Rosati, V. Campagna, F. Montanari, G. Cravotto, and M. Boccalini Synlett 2005 2927
37. G.B. Blackwell, R.N. Haszeldine, and D.R. Taylor J. Chem. Soc., Perkin Trans. 1 1982 2207
38. T. Hanamoto, M. Egashira, K. Ishizuka, H. Furuno, and J. Inanaga Tetrahedron 62 2006 6332
39. S.R.F. Kagaruki, T. Kitazume, and N. Ishikawa Bull. Chem. Soc. Jpn. 54 1981 3221
40. J.-N. Volle, and M. Schlosser Eur. J. Org. Chem. 2000 823
41. Elbe, H.-L.; Rieck, H.; Dunkel, R.; Zhu-Ohlbach, Q.; Mauler-Machnik, A.; Wachendorff-Neumann, U.; Kuck, K.-H. WO 2003/010149.
42. Dietz, J.; Strathmann, S.; Stierl, R.; Montag, J. WO 2007/128756.
43. Nishida, S.; Ohsumi, T.; Tsushima, K.; Matsuo, N.; Maeda, K.; Inoue, S. WO 86/02641
44. McLoughlin, J. I.; Metz, S. WO 93/11117
45. Gallenkamp, B.; Rohe, L.; Marhold, A. EP 776889.
46. J.W. Williams, and J.A. Krynitsky Org. Synth. 21 1941 4