Abstract
A new method of the synthesis of heterocyclic derivatives of trifluoroalanine based on the cyclocondensation of methyl trifluoropyruvate tert-butoxycarbonylimine with C,N- and N,N-binucleophiles, like Nsubstituted ureas, 1-benzyl-6-aminouracil, benzamidine, and 3-aminocrotononitrile, followed by hydrolysis of the resulting Boc-derivatives to 5-amino-5-trifluoromethylimidazolidine-2,4-diones, 5-amino-5-trifluoromethyl-1-benzyl-5,7-dihydropyrrolo[2,3-d]-pyrimidine-2,4,6-3H-trione, 4-amino-2-methyl-5-oxo-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carbonitrile, or 5-amino-5-trifluoromethyl-2-phenyl-3,5-dihydroimidazol-4-one, respectively, was developed.
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Kukhar, V.P. and Soloshonok, V.A., Fluorine-containing Amino Acids: Synthesis and Properties, Chichester: Wiley, 1995, 422 p.
Biomedical Frontiers of Fluorine Chemistry, Ojima, I., McCarthy, J.R., and Welch, J.T., Eds., Washington: ACS Series 639, 1996, p. 42.
Dal Pozzo, A., Dikovskaya, K., Moroni, M., Fagnoni, M., Vanini, R., Bergonzi, R., de Castiglione, P., Bravo, P., and Zanda, M., J. Chem. Res. (S), 1999, no. 8, p. 468.
Koksch, B., Sewald, N., Hofmann, H.-J., Burger, K., and Jakubke, H.-D., J. Pept. Sci., 1997, vol. 3, no. 3, p. 157.
Scolnick, L.R., Clements, A.M., Liao, J., Crenshaw, L., Hellberg, M., May, J., Dean, T.R., and Christianson, D.W., J. Am. Chem. Soc., 1997, vol. 119, no. 4, p. 850.
Sokolov, V.B., Aksinenko, A.Yu., and Martynov, I.V., Russ. Chem. Bull., 2001, no. 6, p. 1113.
Sokolov, V.B., Aksinenko, A.Yu., Goreva, T.V., Epishina, T.A., Pushin, A.N., and Martynov, I.V., Izv. Akad. Nauk, Ser. Khim., 2006, no. 6, p. 1014.
Osipov, S.N., Sokolov, V.B., Kolomiets, A.F., Martynov, I.V., and Fokin, A.V., Russ. Chem. Bull., 1987, no. 5, p. 1098.
Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., and Martynov, I.V., Russ. Chem. Bull., 2005, no. 12, p. 2851.
Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., and Martynov, I.V., Russ. Chem. Bull., 2005, no. 2, p. 470.
Sokolov, V.B., Aksinenko, A.Yu., and Martynov, I.V., Russ. Chem. Bull., 2005, no. 6, p. 1514.
Sokolov, V.B., Aksinenko, A.Yu., and Martynov, I.V., Russ. Chem. Bull., 2007, no. 11, p. 2247.
Osipov, S.N., Shchetnikov, G.T., Zotova, M.A., Bruneau, C., and Dixneuf, P.H., Eur. J. Org. Chem., 2010, no. 8, p. 1587.
Osipov, S.N., Peregudov, A.S., and Shchetnikov, G.T., Synlett, 2007, no. 1, p. 136.
Bolm, C., Husmann, R., Mersmann, S., Raabe, G., Rueping, M., and Sugiono, E., Org. Lett., 2011, vol. 13, no. 5, p. 1044.
Sokolov, V.B. and Aksinenko, A.Yu., Russ. Chem. Bull., 1998, no. 4, p. 727.
Hatzenlaub, W. and Pfleiderer, W., Lieb. Ann. Chem., 1979, no. 11, p. 1847.
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Original Russian Text © V.B. Sokolov, A.Yu. Aksinenko, T.A. Epishina, T.V. Goreva, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 7, pp. 1163–1166.
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Sokolov, V.B., Aksinenko, A.Y., Epishina, T.A. et al. New heterocyclic derivatives of trifluoroalanine. Russ J Gen Chem 84, 1358–1361 (2014). https://doi.org/10.1134/S1070363214070184
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DOI: https://doi.org/10.1134/S1070363214070184