Tributyl(3,3,3-trifluoro-1-propynyl)stannane as an efficient reagent for the preparation of various trifluoromethylated heterocyclic compounds

Tetrahedron Letters

Volumn 45, Issue 41, 2004, Pages 7573-7576

  Hanamoto, Takeshi ^a   Hakoshima, Yuhko ^a   Egashira, Mikio ^a  

^a SAGA UNIVERSITY   (Japan)

Author keywords

1,3 Dipolar cycloaddition; Cross coupling reaction; Isoxazole; Pyrazole; Stannyl acetylene; Triazole; Trifluoromethyl compounds

Indexed keywords

2 BROMO 3,3,3 TRIFLUOROPROPENE; ACETONITRILE; AZIDE; DIAZOMETHANE; HETEROCYCLIC COMPOUND; IODINE; ISOXAZOLE DERIVATIVE; PROPYLENE; PYRAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; TRIBUTYL(3,3,3 TRIFLUORO 1 PROPYNYL)STANNANE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; METHYLATION; STEREOCHEMISTRY;

TRIFLUORO;

EID: 4544264719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.118     Document Type: Article

References (26)

1. T. Hiyama Organofluorine Compounds 2000 Springer New York
2. M. Hudlicky, and A.E. Pavlath Chemistry of Organic Fluorine Compounds II ACS Monograph 187 1995 American Chemical Society Washington, DC
3. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W Collins, S. Doctor, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson J. Med. Chem. 40 1997 1347
4. T. Hanamoto, N. Morita, and K. Shindo Eur. J. Org. Chem. 2003 4279
5. T. Hanamoto, and T. Kobayashi J. Org. Chem. 68 2003 6354
6. T. Hanamoto, K. Handa, and T. Mido Bull. Chem. Soc. Jpn. 75 2002 2497
7. T. Hanamoto, K. Nishiyama, H. Tateishi, and M. Kondo Synlett 2001 1320
8. G. Meazza, and G. Zanardi J. Fluorine Chem. 55 1991 1939
9. G. Meazza, L. Capuzzi, and P. Piccardi Synthesis 9 1989 331
10. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
11. E.T. Bogoradovskii, V.V. Cherkasov, V.S. Zavgorodnii, B.I. Rogozev, and A.A. Petrov Zh. Obshch. Khim. 50 1980 2031 CA 94:47429
12. T. Yamazaki, K. Mizutani, and T. Kitazume J. Org. Chem. 60 1995 6046
13. 3Sn: C, 47.03; H, 7.10. Found: C, 46.71; H, 7.35
14. During the course of our study, the different method for the preparation of 1 was reported, however their method required costly HFC-245fa (1,1,1-3,3-pentafluoropropane) and 3 equiv of n-butyllithium for the generation of the corresponding trifluoropropynyl anion: A.K. Brisdon, I.R. Crossley, R.G. Pritchard, G. Sadiq, and J.E. Warren Organometallics 22 2003 5534
15. 2Sn: C, 45.20; H, 6.88; N, 6.59. Found: C, 45.49; H, 6.79; N, 6.48
16. H. Yamanaka, T. Takekawa, K. Morita, and T. Ishihara Tetrahedron Lett. 37 1996 1829
17. Y. Kobayashi, T. Yamashita, K. Takahashi, H. Kuroda, and I. Kumadaki Chem. Pharm. Bull. 32 1984 4402
18. I. Fleming Frontier Orbitals and Organic Chemical Reactions 1976 John Wiley & Sons New York
19. K.N. Houk, J. Sims, C.R. Watts, and L.J. Luskus J. Am. Chem. Soc. 95 1973 7301
20. X. Han, B.M. Stoltz, and E.J. Corey J. Am. Chem. Soc. 121 1999 7600
21. 2O: C, 56.70; H, 3.57; N, 11.02. Found: C, 56.63; H, 3.55; N, 11.04
22. 3Sn: C, 50.22; H, 6.42; N, 8.37. Found: C, 50.33; H, 6.40; N, 8.42
23. 3NOSn: C, 46.39; H, 6.87; N, 3.18. Found: C, 46.51; H, 6.85; N, 3.20
24. C. Sloop, C.L. Bumgardner, and W.D. Loehle J. Fluorine Chem. 118 2002 135
25. 2: C, 58.00; H, 3.74; N, 5.20. Found: C, 58.24; H, 3.72; N, 5.30
26. G.D. Allred, and L.S. Liebeskind J. Am. Chem. Soc. 118 1996 2748