Abstract
Reactions of 5-aryl- and 5-tert-butyl-3-(benzoylhydrazinylidene)furan-2,3-diones with aromatic and heterocyclic amines afforded 4-aryl-2-(benzoylhydrazinylidene)-4-oxobutanamides and 5,5-dimethyl-2-(benzoylhydrazinylidene)-4-oxohexanamides which exist in solution as mixtures of hydrazone and cyclic dihydropyrazole tautomers.
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Igidov, N.M., Zakhmatov, A.V., and Rubtsov, A.E., Russ. J. Org. Chem., 2016, vol. 52, p. 974.
Igidov, N.M., Kiselev, M.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2016, vol. 52, p. 526.
Zalesov, V.V. and Rubtsov, A.E., Chem. Heterocycl. Compd., 2004, vol. 40, p. 133.
Mayorova, O.A. and Yegorova, A.Y., Magn. Reson. Chem., 2015, vol. 53, p. 853.
Pulina, N.A., Kuznetsov, A.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2015, vol. 51, p. 967.
Maiorova, O.A., Grinev, V.S., and Yegorova, A.Y., J. Struct. Chem., 2015, vol. 56, p. 803.
Maigali, S.S., El-Hussieny, M., and Soliman, F.M., J. Heterocycl. Chem., 2015, vol. 52, p. 15.
Kharitonova, S.S., Igidov, N.M., Zakhmatov, A.V., and Rubtsov, A.E., Russ. J. Org. Chem., 2013, vol. 49, p. 243.
Patel, R.N., Patel, P.V., Desai, K.R., Nimavat, K.S., and Vyas, K.B., Heterocycl. Lett., 2012, vol. 2, no. 3, p. 327.
Gavkus, D.N., Maiorova, O.A., Borisov, M.Yu., and Egorova, A.Yu., Russ. J. Org. Chem., 2012, vol. 48, p. 1229.
Tyuneva, A.V., Igidov, N.M., Koryagina, N.N., Borodin, A.Yu., Zakhmatov, A.V., Makarov, A.S., Toksarova, Yu.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2011, vol. 47, p. 258.
Komarova, O.A., Igidov, N.M., Koryagina, N.N., Makarov, A.S., Toksarova, Yu.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2011, vol. 47, p. 109.
Rubtsov, A.E. and Zalesov, V.V., Bashk. Khim. Zh., 2009, no. 1, p. 49.
Shipilovskikh, S.A., Rubtsov, A.E., and Zalesov, V.V., Chem. Heterocycl. Compd., 2009, vol. 45, p. 658.
Sayed, H.H., Hashem, A.I., Yousif, N.M., and El-Sayed, W.A., Arch. Pharm., 2007, vol. 340, p. 315.
Elkholy, Y.M., Ali, K.A., and Farag, A.M., Phosphorus, Sulfur Silicon Relat. Elem., 2006, vol. 181, p. 2037.
Elkholy, Y.M., Ali, K.A., and Farag, A.M., J. Heterocycl. Chem., 2006, vol. 43, p. 1183.
El-Kousy, S.M., Hashem, A.I., El-Torgoman, A.M., and Salama, G.M., Afinidad, 2003, vol. 503, p. 61.
Rubtsov, A.E. and Zalesov, V.V., Russ. J. Org. Chem., 2003, vol. 39, p. 869.
Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Org. Chem., 2014, vol. 50, p. 1853.
Shipilovskikh, S.A. and Rubtsov, A.E., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, p. 2205.
Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Org. Chem., 2014, vol. 50, p. 298.
Maiorova, O.A. and Egorova, A.Yu., Russ. J. Org. Chem., 2013, vol. 49, p. 1348.
Maiorova, O.A., Babkina, N.V., and Egorova, A.Yu., Chem. Heterocycl. Compd., 2015, vol. 51, p. 517.
Maksimov, E.A., Maiorova, O.A., and Egorova, A.Yu., Russ. J. Org. Chem., 2015, vol. 51, p. 1305.
Rubtsov, A.E., Aliev, Z.G., and Maiorova, O.A., Russ. J. Org. Chem., 2010, vol. 46, p. 933.
Zalesov, V.V., Rubtsov, A.E., and Bystritskaya, O.A., Russ. J. Org. Chem., 2007, vol. 43, p. 1415.
Rubtsov, A.E. and Zalesov, V.V., Russ. J. Org. Chem., 2007, vol. 43, p. 735.
Rubtsov, A.E. and Zalesov, V.V., Chem. Heterocycl. Compd., 2003, vol. 39, p. 541.
Pulina, N.A., Sobin, F.V., Kozhukhar’, V.Yu., Makhmudov, R.R., Rubtsov, A.E., and Naugol’nykh, E.A., Pharm. Chem. J., 2014, vol. 48, no. 1, p. 11.
Pulina, N.A., Kozhukhar’, V.Yu., Makhmudov, R.R., Rubtsov, A.E., and Sheremetev, A.B., Farmatsiya, 2014, no. 5, p. 45.
Pulina, N.A., Zalesov, V.V., Bystritskaya, O.A., Rubtsov, A.E., and Kutkovaya, N.V., Pharm. Chem. J., 2009, vol. 43, no. 8, p. 444.
Rubtsov, A.E., Kovylyaeva, N.V., and Zalesov, V.V., Pharm. Chem. J., 2005, vol. 39, no. 1, p. 11.
Rubtsov, A.E., Makhmudov, R.R., Kovylyaeva, N.V., Prosyanik, N.I., Bobrov, A.V., and Zalesov, V.V., Pharm. Chem. J., 2002, vol. 36, no. 11, p. 608.
Shipilovskikh, S.A., Makhmudov, R.R., Lupach, D.Yu., Pavlov, P.T., Babushkina, E.V., and Rubtsov, A.E., Pharm. Chem. J., 2013, vol. 47, no. 7, p. 366.
Herk, T., Brussee, J., Nieuwendijk, A.M.C.H., Klein, P.A.M., Ijzerman, A.P., Stannek, C., Burmeister, A., and Lorenzen, A., J. Med. Chem., 2003, vol. 46, no. 18, p. 3945.
Frank, A.O., Feldkamp, M.D., Kennedy, J.P., Waterson, A.G., Pelz, N.F., Patrone, J.D., Vangamudi, B., Camper, D.V., Rossanese, O.W., Chazin, W.J., and Fesik, S.W., J. Med. Chem., 2013, vol. 56, no. 22, p. 9242.
Liu, G., Xin, Z., Pei, Z., Hajduk, P.J., Abad-Zapatero, C., Hutchins, C.W., Zhao, H., Lubben, T.H., Ballaron, S.J., Haasch, D.L., Kaszubska, W., Rondinone, C.M., Trevillyan, J.M., and Jirousek, M.R., J. Med. Chem., 2003, vol. 46, no. 20, p. 4232.
Sechi, M., Innocenti, A., Pala, N., Rogolino, D., Carcelli, M., Scozzafava, A., and Supuran, C.T., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 18, p. 5801.
Cvijetiæ, I.N., Tanç, M., Juraniæ, I.O., Verbiæ, T.Ž., Supuran, C.T., and Drakuliæ, B.J., Bioorg. Med. Chem., 2015, vol. 23, no. 15, p. 4649.
Yakimovich, S.I., Nikolaev, V.N., and Kutsenko, E.Yu., Zh. Org. Khim., 1982, vol. 18, p. 762.
Yakimovich, S.I. and Zerova, I.V., Zh. Org. Khim., 1980, vol. 16, p. 1633.
Yakimovich, S.I., Zerova, I.V., and Gavrilova, N.N., Zh. Org. Khim., 1977, vol. 13, p. 263.
Yakimovich, S.I. and Zerova, I.V., Zh. Org. Khim., 1978, vol. 14, p. 42.
Pakal’nis, V.V., Zerova, I.V., Yakimovich, S.I., and Alekseev, V.V., Chem. Heterocycl. Compd., 2013, vol. 49, p. 408.
Pakal’nis, V.V., Zerova, I.V., and Yakimovich, S.I., Russ. J. Gen. Chem., 2007, vol. 77, p. 1732.
Yakimovich, S.I. and Nikolaev, V.N., Zh. Org. Khim., 1981, vol. 17, p. 284.
Koz’minykh, V.O., Goncharov, V.I., Koz’minykh, E.N., and Oborin, D.B., Chem. Heterocycl. Compd., 2006, vol. 42, p. 692.
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Original Russian Text © M.A. Kiselev, N.M. Igidov, I.N. Chernov, Yu.S. Toksarova, A.E. Rubtsov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 6, pp. 903–908.
For communication XIII, see [1].
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Kiselev, M.A., Igidov, N.M., Chernov, I.N. et al. Chemistry of iminofurans: XIV. Ring opening of 5-substituted furan-2,3-dione 3-benzoylhydrazones by the action of aromatic and heterocyclic amines. Russ J Org Chem 53, 920–925 (2017). https://doi.org/10.1134/S1070428017060173
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DOI: https://doi.org/10.1134/S1070428017060173