Abstract
Azo coupling of fluorinated 1,3-diketones with 4-ethoxycarbonyl-1H-imidazole-5-diazonium chloride led to the formation of 4-hydroxy-4-polyfluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines. According to the 1H and 19F NMR data, these compounds in solution give rise to ring-chain tautomerism via opening of the C4-N5 bond, which is especially characteristic of dihydroimidazotriazines with a polyfluoroalkyl substituent longer than trifluoromethyl group.
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Tennant, G., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1982, vol. 3, p. 482; Haikala, H.O., Nore, P.T., Honkanen, E.J., Pystynen, J.J., Lonnberg, K.K., Luiro, A.M., and Pippuri, A.K., EU Patent no. 383 449, 1990; Chem. Abstr., 1991, vol. 114, no. 81 895 t; Haikala, H.O., Honkanen, E.J., Lonnberg, K.K., Nore, P.T., Pystynen, J.J., Luiro, A.M., and Pippuri, A.K., UK Patent no. 2 228 004, 1990; Chem. Abstr., 1991, vol. 114, no. 228 967 d; Farghaly, A.M., El-Khwass, S.M., Khalil, M.A., Sharabi, F.M., and Daabees, T.T., Pharmazie, 1981, vol. 36, p. 93; Ismaiel, A.M., Yousif, M.Y., Metwally, M.A., and El-Kerdawy, M., Indian J. Chem., Sect. B, 1986, vol. 25, p. 1238.
Tennant, B.G. and Vevers, J.S., J. Chem. Soc., Perkin Trans. 1, 1976, p. 421; Mackie, H. and Tennant, G., Tetrahedron Lett., 1972, vol. 13, p. 4719; Partridge, M.W. and Stevens, M.F.G., J. Chem. Soc. C, 1966, p. 1127; Elnagdi, M.H., El-Moghayar, M.R.H., Fleita, D.H., Hafez, E.A.A., and Fahmy, S.M., J. Org. Chem., 1976, vol. 41, p. 3781; Elnagdi, M.H., Zayed, E.M., El-Sayed Khalifa, M.A., and Ghozlan, S.A., Monatsh. Chem., 1981, vol. 112, p. 245; Elnagdi, M.H., Taha, N.H., Abd El All, F.A.M., Abdel-Motaleb, R.M., and Mahmoud, F.F., Collect. Czech. Chem. Commun., 1989, vol. 54, p. 1082; Allmann, R., Debaer-Demaeker, T., Grahn, W., and Reichardt, C., Chem. Ber., 1974, vol. 107, p. 1555; Golec, J.M.C., Scrowston, R.M., and Dunleavy, M., J. Chem. Soc., Perkin Trans. 1, 1992, p. 239; Bedford, G.R., Cooper, F.C., Partridge, M.W., and Stevens, M.F.G., J. Chem. Soc., 1963, p. 5901.
Khudina, O.G., Shchegol’kov, E.V., Burgart, Ya.V., Kodess, M.I., Kazheva, O.N., Chekhlov, A.N., Shilov, G.V., Dyachenko, O.A., Saloutin, V.I., and Chupakhin, O.N., J. Fluorine Chem., 2005, vol. 126, p. 1230.
Baig, G.U. and Malcolm, M.F.G., J. Chem. Soc., Perkin Trans. 1, 1981, p. 1424; Baig, G.U. and Stevens, M.F.G., J. Chem. Soc., Perkin Trans. 1, 1987, p. 665; Novinson, T., Okabe, T., Robins, R.K., and Matthews, T.R., J. Med. Chem., 1976, vol. 19, p. 517; Sadchikova, E.V. and Mokrushin, V.S., Vestn. Ural. Gos. Tekh. Univ.-Ural. Politekh. Inst., Ser. Khim., 2003, p. 85.
Berezov, T.T. and Korovkin, B.F., Biologicheskaya khimiya (Biological Chemistry), Moscow: Meditsina, 1998.
Crew, A.P., Mulvihill, M.J., and Werner, D.S., WO Patent no. 2006-012 422, 2006.
Erguden, J.K., Bauser, M., Burkhardt, N., Flubacher, D., Friedl, A., Gerlach, I., Hinz, V., Jork, R., Naab, P., Niewohner, U., Repp, T.O., Schlemmer, K.-H., Stoltefuss, J., Bruckner, D., Hedrix, M., Schauss, D., and Tersteegen, A., WO Patent no. 2003-000 693, 2003.
Structure Determination of Organic Compounds. Tables of Spectral Data, Pretsch, E., Bühlmann, P., and Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed. Translated under the title Opredelenie stroeniya organicheskikh soedinenii. Tablitsy spektral’nykh dannykh, Moscow: Mir, BINOM, 2006, p. 294.
Kuzueva, O.G., Burgart, Ya.V., and Saloutin, V.I., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, p. 695; Burgart, Ya.V., Fokin, A.S., Kuzueva, O.G., Chupakhin, O.N., and Saloutin, V.I., J. Fluorine Chem., 1998, vol. 92, p. 101.
Shchegol’kov, E.V., Burgart, Ya.V., Khudina, O.G., Saloutin, V.I., and Chupakhin, O.N., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 2478.
Khudina, O.G., Shchegol’kov, E.V., Burgart, Ya.V., Kodess, M.I., Saloutin, V.I., Kazheva, O.N., Shilov, G.V., D’yachenko, O.A., Grishina, M.A., Potemkin, V.A., and Chupakhin, O.N., Russ. J. Org. Chem., 2007, vol. 43, p. 380.
Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases, London: Methuen, 1962.
Scheldrik, G.M., SHELXS 97, SHELXL 97, Göttingen: Univ. of Göttingen, Germany, 1997.
Pashkevich, K.I., Saloutin, V.I., and Postovskii, I.Ya., Usp. Khim., 1981, vol. 50, p. 326.
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Original Russian Text © E.V. Shchegol’kov, E.V. Sadchikova, Ya.V. Burgart, V.I. Saloutin, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 4, pp. 586–594.
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Shchegol’kov, E.V., Sadchikova, E.V., Burgart, Y.V. et al. Synthesis and structure of 4-hydroxy-4-fluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines. Russ J Org Chem 45, 572–580 (2009). https://doi.org/10.1134/S1070428009040174
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DOI: https://doi.org/10.1134/S1070428009040174