Beilstein J. Org. Chem. 2013, 9, 2387–2394.
8. Dallanoce, C.; Frigerio, F.; Martelli, G.; Grazioso, G.; Matera, C.;
Pomè, D. Y.; Pucci, L.; Clementi, F.; Gotti, C.; De Amici, M.
Bioorg. Med. Chem. 2010, 18, 4498–4508.
Conclusion
In conclusion, we have developed a simple, mild and efficient
one-step procedure for the synthesis of functionalized 3-tri-
fluoromethyl-2-isoxazolines and 3-trifluoromethyl-2-isoxa-
zoles from trifluoromethyl aldoxime 2 by utilizing DIB as
oxidant. The applicability of the 3-trifluoromethyl-2-isoxazo-
lines to supply different fluorinated building blocks was demon-
strated by the easy ring opening of these intermediates with
NaBH4 and NiCl2, yielding the corresponding trifluoro-
methylated γ-amino alcohol.
9. Cheng, J.-F.; Huang, Y.; Penuliar, R.; Nishimoto, M.; Liu, L.;
Arrhenius, T.; Yang, G.; O'Leary, E.; Barbosa, M.; Barr, R.;
Dyck, J. R. B.; Lopaschuk, G. D.; Nadzan, A. M. J. Med. Chem. 2006,
10.Benltifa, M.; Hayes, J. M.; Vidal, S.; Gueyrard, D.; Goekjian, P. G.;
Praly, J.-P.; Kizilis, G.; Tiraidis, C.; Alexacou, K.-M.; Chrysina, E. D.;
Zographos, S. E.; Leonidas, D. D.; Archontis, G.; Oikonomakos, N. G.
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11.Rakesh; Sun, D.; Lee, R. B.; Tangallapally, R. P.; Lee, R. E.
Eur. J. Med. Chem. 2009, 44, 460–472.
Supporting Information
Supporting Information File 1
12.Tangallapally, R. P.; Sun, D.; Rakesh; Budha, N.; Lee, R. E. B.;
Lenaerts, A. J.; Meibohm, B.; Lee, R. E. Bioorg. Med. Chem. Lett.
13.Tang, S.; He, J.; Sun, Y.; He, L.; She, X. J. Org. Chem. 2010, 75,
General methods, synthetic procedure, spectroscopic data,
1H NMR, 13C NMR and 19F NMR of compounds of 2,
1a-1j, 1l-1n, 7a, 7b, 6 and computational results.
14.Jiang, D.; Chen, Y. J. Org. Chem. 2008, 73, 9181–9183.
15.Maimone, T. J.; Shi, J.; Ashida, S.; Baran, P. S. J. Am. Chem. Soc.
16.Chambers, R. D. Fluorine in Organic Chemistry; Blackwell Publishing
Acknowledgements
R.S.B.G thanks the FAPERJ, CNPq, the Marie Curie program,
the Farmaguinhos/FioCruz, and PGQu for financial support.
Central Glass Co. Ltd. is gratefully acknowledged for kindly
providing fluoral hydrate and HFIP, as well as the IT depart-
ment from Université Paris-Sud for providing computing
resources. The authors would like thank M’bokeno Gomes
Lowa, Erasmus student. We also thank the French Fluorine
Network (GIS Fluor).
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