Abstract
An efficient one-pot procedure has been proposed for the synthesis of compounds containing three carboxamide groups or one carboxamide and two ester groups. The procedure is based on three-component condensation of alkyl isocyanides with 5-alkylidene- or 5-arylmethylene-substituted Meldrum's acids in the presence of such nucleophiles as phenols and amines.
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REFERENCES
Chen, B.-</del>C., Heterocycles, 1991, vol. 32, p. 529.
McNab, H., Chem. Soc. Rev., 1978, vol. 7, p. 345.
Stevenson, R. and Weber, J.V., Heterocycles, 1988, vol. 27, p. 1929.
Bitter, J., Leitich, J., Partale, H., Polansky, O.E., Riemer, W., Ritter-Thomas, U., Schlamann, B., and Stilkerieg, B., Chem. Ber., 1980, vol. 113, p. 1020.
Tietze, L.F. and Kiedrowski, G.V., Tetrahedron Lett., 1981, vol. 22, p. 219.
Takano, S., Satoh, S., and Ogasawara, K., Heterocycles, 1985, vol. 23, p. 41.
Shaabani, A. and Farrokhzad, F., J. Chem. Res., Synop., 1997, p. 344.
Yavari, I., Shaabani, A., and Maghsoodlou, M.T., Monatsh. Chem., 1997, vol. 128, p. 697.
Yavari, I., Shaabani, A., Asghari, S., Olmsted, M., and Safari, N., J. Fluorine Chem., 1997, vol. 86, p. 77.
Shaabani, A., Ajabi, S., Farrokhzad, F., and Bijanzadeh, H.M., J. Chem. Res., Synop., 1999, p. 582.
Shaabani, A., Yavari, I., Teimouri, M.B., Bazgir, A., and Bijanzadeh, H.M., Tetrahedron, 2001, vol. 57, p. 1375.
Shaabani, A. and Teimouri, M.B., J. Chem. Res., Synop., 2002, p. 433.
Hiratani, K., US Patent no. 5 071 989, 1991.
Mohapatara, P.K., Sriram, S., and Badheka, L.P., Sep. Sci. Technol., 2000, vol. 35, p. 39.
Chan Gabriel, Y.S., Drew, M.G.B., and Madic, C., J. Chem. Soc., Dalton Trans., 1997, p. 649.
Iveson, P.B., Drew, M.G.B., and Madic, C., J. Chem. Soc., Dalton Trans., 1999, p. 3605.
Hiratani, K. and Taguchi, K., Chem. Lett., 1989, p. 2073.
Darling, C.M., US Patent no. 4 537 781, 1985.
Jursic, B.S., Tetrahedron Lett., 2000, vol. 41, p. 5325.
Beckwith, A.L.J., The Chemistry of Amides., Zabicky, J., Ed., London: Intersci., 1970, p. 74.
Hedge, J.A., Kruse, C.W., and Snyder, H.R., J. Org. Chem., 1961, vol. 26, p. 3166.
Bihlmayer, G.A., Derflinger, G., Derkosch, J., and Polansky, O.E., Monatsh. Chem., 1967, vol. 98, p. 564.
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Shaabani, A., Teimouri, M.B. & Bijanzadeh, H.R. An Efficient One-Pot Synthesis of Triamides and Amidodiesters. Russian Journal of Organic Chemistry 40, 976–981 (2004). https://doi.org/10.1023/B:RUJO.0000045188.81414.1d
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DOI: https://doi.org/10.1023/B:RUJO.0000045188.81414.1d