Abstract
Methods have been developed for the synthesis of a series of nitrogen-containing derivatives of fumaropimaric acid, in particular triamides, amido amidines, and amido diesters. New functionalized derivatives at the 11- and 12-positions (diol, bis-methanesulfonate, bis-p-toluenesulfonate, diazide, and bis-triazoles) have been synthesized from the 1-(piperidin-1-ylcarbonyl) derivative.
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References
Halbrook, N.J. and Lawrence, R.V., J. Am. Chem. Soc., 1958, vol. 80, p.368.
Wiyono, B. and Tachibana, S., Pak. J. Biol. Sci., 2008, vol. 11, p. 1884.
Wiyono, B., Tachibana, S., and Tinambunan, D., Pak. J. Biol. Sci., 2007, vol. 10, p. 1588.
Ayer, W.A. and McDonald, C.E., Can. J. Chem., 1965, vol. 43, p. 1429.
Lee, J.S. and Hong, S.I., Eur. Polym. J., 2002, vol. 38, p.387.
Zalkow, L.H., Kulkarni, M.V., and Girotra, N.N., J. Org. Chem., 1965, vol. 30, p. 1679.
Tolstikov, A.G., Karpushev, N.N., Tolstikova, O.V., Khlebnikova, T.B., Sal’nikov, G.E., Mamatyuk, V.I., Gatilov, Yu.V., and Bagryanskaya, I.Yu., Russ. J. Org. Chem., 2001, vol. 37, p. 1134.
Lianli, D., Chengyong, H., Chunning, S., Baowen, Z., Jing, Y., Minmin, S., and Jianqiang, M., Ind. Eng. Chem. Res., 2013, vol. 52, p. 13233.
Song, X. and Zhou, Y., Huaxue Shiji, 2011, vol. 33, no. 5, p.445.
Konev, V.N., Khlebnikova, T.B., and Pai, Z.P., Khim. Interesakh Ustoich. Razvit., 2011, vol. 19, p.165.
Wang, H., Tian, X., Yang, D., Pan, Y., Wu, Q., and He, C., Tetrahedron: Asymmetry, 2011, vol. 22, p.381.
Xu, X., Song, Z., Shang, S., Cui, S., and Rao, X., Polym. Int., 2011, vol. 60, p. 1521.
Glovsky, M.M., Becker, E.L., and Halbrook, N.J., J. Immunol., 1968, vol. 100, p.989.
Glovsky, M.M., Ward, P.A., and Fudenberg, H.H., Clin. Immunol. Immunopathol., 1973, vol. 1, no. 2, p.165.
Tanaka, R., Tokuda, H., and Ezaki, Y., Phytomedicine, 2008, vol. 15, p.985.
Glanzer, J.G., Liu, S., and Oakley, G.G., Bioorg. Med. Chem., 2011, vol. 19, p. 2589.
Glanzer, J.G., Carnes, K.A., Soto, P., Liu, S., Parkhurst, L.J., and Oakley, G.G., Nucleic Acids Res., 2013, vol. 41, p. 2047.
Bei, M.P. and Yuvchenko, A.P., Izv. Nats. Akad. Nauk Belarusi, Ser. Khim. Nauk, 2010, no. 3, p.84.
Sinott, M., Carbohydrate Chemistry and Biochemistry: Structure and Mechanism, Cambridge: RCS, 2007, p.579.
Liang, L. and Astruc, D., Coord. Chem. Rev., 2011, vol. 255, p. 2933.
The Chemistry of Amidines and Imidates, Patai, S., Ed., London: Wiley, 1975.
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Original Russian Text © M.P. Bei, A.P. Yuvchenko, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 468–476.
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Bei, M.P., Yuvchenko, A.P. Synthesis of New Nitrogen-Containing Derivatives of Fumaropimaric Acid. Russ J Org Chem 54, 475–484 (2018). https://doi.org/10.1134/S1070428018030168
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DOI: https://doi.org/10.1134/S1070428018030168