Abstract
Reactions of 2-diazo-1,1,1-trifluoro-3-nitropropane or 1-trifluoromethyl-2-nitroethenes with amines and amino alcohols afforded N-mono- and N,N-disubstituted α-trifluoromethyl β-nitro amines, which were used to obtain a number of trifluoromethyl-containing 1,2-diamines, amino alcohols, and β-amino acids.
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References
N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, 392 pp.
D. Lucet, S. Sabelle, O. Kostelitz, T. Le Gall, C. Mioskowski, Eur. J. Org. Chem., 1999, 2583.
S. Sabelle, D. Lucet, T. Le Gall, C. Mioskowski, Tetrahedron Lett., 1998, 39, 2111.
J. C. Anderson, S. Peace, S. Pih, Synlett., 2000, 850.
J. Turconi, L. Lebeau, J.-M. Paris, C. Mioskowski, Tetrahedron, 2006, 62, 8109.
A. Ya. Aizikovich, I. N. Sheptun, Zh. Org. Khim., 1985, 21, 2212 [J. Org. Chem. USSR (Engl. Transl.), 1985, 21].
A. Ya. Aizikovich, V. Yu. Korotaev, V. A. Sagaidak, Zh. Org. Khim., 1998, 34, 832 [Russ. J. Org. Chem. (Engl. Transl.), 1998, 34, 782].
RF Pat. 2 131 410; Byull. Izobret., 1999, 408.
J. Turconi, L. Lebeau, J.-M. Paris, C. Mioskowski, Tetrahedron Lett., 2006, 47, 121.
V. Yu. Korotaev, Yu. A. Skorik, A. Yu. Barkov, M. I. Kodess, A. Ya. Zapevalov, Izv. Akad. Nauk, Ser. Khim., 2005, 2465 [Russ. Chem. Bull., Int. Ed., 2005, 54, 2545].
A. Ya. Aizikovich, V. Yu. Korotaev, Zh. Org. Khim., 1999, 35, 226 [Russ. J. Org. Chem. (Engl. Transl.), 1999, 35, 207].
A. Ya. Aizikovich, M. V. Nikonov, M. I. Kodess, V. Yu. Korotaev, V. N. Charushin, O. N. Chupakhin, Tetrahedron, 2000, 56, 1923.
V. Ya. Sosnovskikh, V. A. Kutsenko, A. Ya. Aizikovich, V. Yu. Korotaev, Izv. Akad. Nauk, Ser. Khim., 1999, 2135 [Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 2112].
A. Ya. Aizikovich, I. T. Bazyl’, Zh. Org. Khim., 1987, 23, 1330 [J. Org. Chem. USSR (Engl. Transl.), 1987, 23].
H. Shechter, D. E. Ley, E. B. Roberson, J. Am. Chem. Soc. 1956, 78, 4984.
E. T. McBee, C. E. Hathaway, C. W. Roberts, J. Am. Chem. Soc., 1956, 78, 4053.
Ya. Shen, G. Wang, J. Ni, J. Sun, Synthesis, 2003, 1574.
A. T. Blomquist, T. H. Shelley, J. Am. Chem. Soc., 1948, 70, 147.
N. Takamura, T. Mizoguchi, Tetrahedron Lett., 1973, 14, 4267.
M. Regitz, S. G. Khbeis, Chem. Ber., 1984, 117, 2233.
J. G. Lee, K. I. Choi, H. Y. Koh, Y. Kim, Y. Kang, Y. S. Cho, Synthesis, 2001, 81.
V. V. Perekalin, Zh. Org. Khim., 1985, 21, 1111 [J. Org. Chem. USSR(Engl. Transl.), 1985, 21].
J. O. Osby, B. Ganem, Tetrahedron Lett., 1985, 26, 6413.
G. M. Dubowchik, J. A. Michne, D. Zuev, Bioorg. Med. Chem. Lett., 2004, 14, 3147.
A. Murray, D. L. Willams, in Organic Synthesis with Isotopes. Part II. Compounds of Isotopic Hydrogen, Interscience Publ., New York, 1958.
G. M. Sheldrick, SHELX-97, Programs for Crystal Structure Determination and Refinement, University of Göttingen, Göttingen (Germany), 1997.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1827–1838, September, 2009.
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Korotaev, V.Y., Barkov, A.Y., Kodess, M.I. et al. N-Substituted α-trifluoromethyl β-nitro amines in the synthesis of fluorine-containing 1,2-diamines, amino alcohols, and β-amino acids. Russ Chem Bull 58, 1886–1898 (2009). https://doi.org/10.1007/s11172-009-0257-2
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DOI: https://doi.org/10.1007/s11172-009-0257-2