Abstract
The reactions of 3-amino-1-phenyl-and 3-amino-1-(thien-2-yl)-4,4,4-trifluorobut-2-en-1-ones with 1,2-diaminopropane under kinetically controlled conditions afford mixtures ofcis andtrans isomers of 2-aroylmethyl-4-methyl-2-trifluoromethylimidazolidines. Analogous reactions with 1,2-diamino-3,3,3-trifluoropropane yieldcis-2-aroylmethyl-2,4-bis(trifluoro-methyl)imidazolidines.
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K. I. Pashkevich, A. Ya. Aizikovich, and I. Ya. Postovskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 455 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981,30 (Engl. Transl.)].
K. N. Zelenin and I. V. Ukraintsev,Org. Prep. Proced. Int., 1998,30, 109.
G. Crank, D. R. K. Harding, and S. S. Szinai,J. Med. Chem., 1970,13, 1212.
G. Crank, D. R. K. Harding, and S. S. Szinai,J. Med. Chem., 1970,13, 1215.
V. Ya. Sosnovskikh and M. Yu. Morozov,Khim. Geterotsikl. Soedin., 1998, 847 [Chem. Heterocycl. Compd., 1998 (Engl. Transl.)].
V. Ya. Sosnovskikh and V. A. Kutsenko,Izv. Akad. Nauk, Ser. Khim., 1999, 546 [Russ. Chem. Bull., 1999,48, 540 (Engl. Transl.)].
A. Ya. Aizikovich, V. Yu. Korotaev, and A. Yu. Barkov,Int. Memorial I. Postovsky Conf. on Organic Chemistry. Ekaterinburg, 1998, 43.
F. A. L. Anet,J. Am. Chem. Soc., 1962,84, 747.
G. M. J. Slusarczuk and M. M. Joullie,J. Org. Chem., 1971,36 37.
A. Ya. Aizikovich, V. Yu. Korotaev, M. I. Kodess, and A. Yu. Barkov,Zh. Org. Khim., 1998,34, 383 [Russ. J. Org. Chem., 1998,34 (Engl. Transl.)].
H. Günther, NMRSpectroscopy. An Introduction, J. Wiley and Sons, New York, 1980.
S. Proskov, H. E. Simmons, and T. L. Cairns,J. Am. Chem. Soc., 1966,88, 5254.
A. Ya. Aizikovich and I. N. Sheptun,Zh. Org. Khim., 1985,21, 2212 [J. Org. Chem. USSR, 1984,21 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2135–2139, November, 1999.
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Sosnovskikh, V.Y., Kutsenko, V.A., Aizikovich, A.Y. et al. Reactions of 3-amino-1-phenyl- and 3-amino-1-(thien-2-yl)-4,4,4-trifluorobut-2-en-1-ones with 1,2-diaminopropane and 1,2-diamino-3,3,3-trifluoropropane. Russ Chem Bull 48, 2112–2116 (1999). https://doi.org/10.1007/BF02494858
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DOI: https://doi.org/10.1007/BF02494858