Abstract
Condensation of methyl (3-hydroxyphenyl)carbamate with ethyl acetoacetate and ethyl benzoylacetate at room temperature, as well as with L-2-hydroxysuccinic acid on heating, in the presence of concentrated sulfuric acid gave the corresponding methyl (4-R-2-oxo-2H-chromen-7-yl)carbamates (R = Me, Ph, H). Condensation of methyl (3-hydroxyphenyl)carbamate with benzylidenemalononitrile or with aromatic aldehydes and malononitrile on heating in propan-2-ol in the presence of piperidine led to the formation of the corresponding methyl (4-aryl-2-amino-3-cyano-4H-chromen-7-yl)carbamates.
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Melekhin, E.A., Bardasov, I.N., Ershov, O.V., and Kayukov, Ya.S., Khimiya i biologicheskaya aktivnost’ sinteticheskikh i prirodnykh soedinenii. Azotsoderzhashchie geterotsikly (Chemistry and Biological Activity of Synthetic and Natural Compounds. Nitrogen-Containing Heterocycles), Kartsev, V.G., Ed., Moscow: MBFNP, 2006, vol. 2, p. 191.
Imasheva, N.M., Kovalev, V.B., and Velikorodov, A.V., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 2006, vol. 49, p. 23.
Elgemeie, G.E.H., Sallam, M.M.M., Sherif, S.M., and Elnagdi, M.H., Heterocycles, 1985, vol. 23, p. 3107.
Elagamey, A.G.A., Sawllim, S.Z., El-Tawell, M.A., and Elnagdi, M.H., Collect. Czech. Chem. Commun., 1988, vol. 53, p. 1534.
Elagamey, A.G.A. and El-Tawell, M.A., Indian J. Chem., Sect. B, 1990, p. 29.
Velikorodov, A.V., Bakova, O.V., and Mochalin, V.B., Russ. J. Org. Chem., 2002, vol. 38, p. 66.
Cross B., Aronti R.L. US Patent no. 3 852 332, 1974; Chem. Abstr., 1974, vol. 82, no. 139 732 b.
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Original Russian Text © A.V. Velikorodov, N.M. Imasheva, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 9, pp. 1389–1392.
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Velikorodov, A.V., Imasheva, N.M. Synthesis of carbamate derivatives of coumarin and chromene. Russ J Org Chem 44, 1374–1377 (2008). https://doi.org/10.1134/S1070428008090212
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DOI: https://doi.org/10.1134/S1070428008090212