Abstract
Condensation of methyl N-(3-hydroxyphenyl)carbamate with ethyl trifluoromethylacetoacetate, 2-methoxyethyl acetoacetate in the presence of conc. sulfuric acid, and also with acetonedicarboxylic acid formed in situ from citric acid under the action of conc. sulfuric acid afforded chromene derivatives. The esterification of 2-{7-[(methoxycarbonyl)amino]-2-oxo-2H-chromen-4-yl}acetic acid with methanol in the presence of TsOH provided the corresponding ester. The oxidation of its α-methylene group with selenium dioxide led to the formation of methyl 2-{7-[(methoxycarbonyl)amino]-2-oxo-2H-chromen-4-yl}-2-oxo-acetate entering into a condensation with o-phenylenediamine resulting in a derivative with a dihydroquinoxaline fragment. The reaction of phenyl N-(4-formylphenyl)carbamate with 3-acetyl-2H-chromen-2-one in butanol in the presence of catalytic quantity of piperidine and acetic acid furnished 4-[(E)-3-oxo-2H-chromen-3-yl)-1-propenyl]phenyl N-phenylcarbamate.
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Symeonidis, T., Fylaktakidou, K.S., Hadjipavlou-Litina, D.J., and Litinas, K.E., Eur. J. Med. Chem., 2009, vol. 44, p. 5012.
Rajamanickam, V., Subburaju, T., Lakshminarayanan, B., and Pradeep Rajkumar, L.A., E.-J. Chem., 2010, vol. 7, p. 383.
MladenoviĆ, M., VukoviĆ, N., Sukdolak, S., and SolujiĆ, S. Molecules, 2010, vol. 15, p. 4294.
Ajani, O.O., and Nwinyi, O.C., J. Heterocyclic Chem., 2010, vol. 47, p. 179.
Kesten, S.R., Heffner, T.G., Johnson, S.J., Pugsley, T.A., Wright, J.L., and Wise, L.D., J. Med. Chemi., 1999, vol. 42, p. 3718.
Kumar, P.V., and Rao, V.R., Indian J. Chem., 2008, vol. 47B, p. 106.
LakshmiNarayanan, B., Pradeep Rajkumar, L.A., Arulanandham, A., Satheesh Babu, N., Gayathri, T., and Raju, A., Int. J. Pharm. Sci. Res., 2012, vol. 3, p. 474.
Arshad, A., Osman, H., Bagley, M.C., Lam, C.K., Mohamad, S., and Zahariluddin, A.S.M., Eur. J. Med. Chem., 2011, vol. 46, p. 3788.
Velikorodov, A.V., and Ishmaeva, N.M., Russ. J. Org. Chem., 2008, vol. 44, p. 1374.
Ishmaeva, N.M., Velikorodov, A.V., and Krivosheev, O.O., Russ. J. Org. Chem., 2008, vol. 44, p. 1649.
Mashelkar, U.C., and Audi, A.A., J. Indian Chem. Soc., 2006, vol. 45B, p. 967.
Habibi, D., Zolfigol, M.A., and Safaee, M., J. Chem., 2013, p. 1.
Sahu, S.K., Mishra, A., and Behera, R.K., Indian J. Heterocyclic. Chem., 1996, vol. 6, p. 91.
Aragade, P., Maddi, V., Khode, S., Palkar, M., Ronad, P., Mamledesai, S., and Satyanarayana, D., Arch. Pharm. Chem. Life Sci., 2009, vol. 342, p. 361.
Arbuzova, S.N., Glotova, T.E., Dvorko, M.Yu., Ushakov, I.A., Gusarova, N.K., and Trofimov, B.A., Arkivoc, 2011, vol. xi, p. 183.
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Original Russian Text © A.V. Velikorodov, V.A. Ionova, E.A. Melent’eva, N.N. Stepkina, A.A. Starikova, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 8, pp. 1131–1135.
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Velikorodov, A.V., Ionova, V.A., Melent’eva, E.A. et al. Synthesis of aromatic carbamates derivatives with a chromen-2-one fragment. Russ J Org Chem 50, 1112–1116 (2014). https://doi.org/10.1134/S1070428014080077
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DOI: https://doi.org/10.1134/S1070428014080077