Abstract
Condensation of methyl N-(4-acetylphenyl)carbamate with aromatic aldehydes in basic and acid environment, and also with hetarylaldehydes in the presence of bases afforded chalcones with the carbamate function. Under the conditions of basic catalysis a nucleophilic substitution was observed of a methoxy group in the carbamate moiety of the chalcone for an ethoxy group. The reactions of the obtained chalcones with hydrazine hydrate, isonicotinic acid hydrazide, guanidine and hydroxylamine hydrochlorides, thiourea, and selenium dioxide furnished the corresponding derivatives of pyrazole, oxazole, pyrimidine, and selenadiazole.
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References
Dhar, D.N. and Lal, J.B., J. Org. Chem., 1958, vol. 23, p. 1159.
Fujise, S. and Tatsuta, H. J. Chem. Soc. Jpn., 1942, vol. 63, p. 632.
Daskiewicz, J.B., Comte, G., Barron, D., Di Pietro, A., and Thomasson, F., Tetrahedron Lett., 1999, vol. 40, p. 7095.
Sutariya, B., Raziya, S.K., Mohan, S., and Sambasiva, S.V., Indian, J. Chem., 2007, vol. 46B, p. 884.
Barral, K., Moorhouse, A.D., and Moses, J.E., Org. Lett., 2007, vol. 9, p. 1809.
Calloway, N.O. and Green, L.D., J. Am. Chem. Soc., 1937, vol. 59, p. 809.
Breslow, D.S. and Hauser, C.R., J. Am. Chem. Soc., 1940, vol. 62, p. 2385.
Szell, T. and Sohar, I., Can. J. Chem., 1969, vol. 47, p. 1254.
Iranpoor, N. and Kazemi, F., Tetrahedron, 1998, vol. 54, p. 9475.
Konieczny, M.T., Konieczny, W., Sabisz, M. Skladanowski, A., Wakiec, R., Augustynowicz-Kopec, E., and Zwolska, Z., Eur. J. Med. Chem., 2007, vol. 42, p. 729.
Kumar, D., Kumar, N.M., Akamatsu, K., Kusaka, E., Harada, H., and Ito, T., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 3916.
Ducki, S., Forrest, R., Hadfield, J.A., Kendall, A., Lawrence, N.J., McGrown, A.T., and Rennison, D., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 1051.
Wegmuller, M., von der Wied, J.P., Oberson, P., Gisin, N., Edenhar-der, R., Petersdorff, I.V., and Rauscher, R., Mutat. Res., 1993, vol. 9, p. 261.
Pandeya, S.N., Sriram, D., Nath, G., and DeClercq, E., Eur. J. Ved. Chem., 1999, vol. 9, p. 25.
Biradar, J.S., Sasidhar, B.S. and Parveen, R., J. Med. Chem., 2010, vol. 45, p. 4074.
Nowakowska, Z., Eur. J. Med. Chem., 2007, vol. 42, p. 125.
Cherkupally, S.R., Dassari, C.R., Vookanti, Y., and Adki, N., Org. Commun., 2010, vol. 3, p. 57.
Sabzevari, O., Mahmoudian, S., Minaei, B., and Paydar, H., Toxicol. Lett., 2010, 196, p. 213.
Arsenyan, P., Pudova, O., and Lukevics, E., Tetrahedron Lett., 2002, vol. 43, p. 4817.
Regitz, M. and Krill, S., Phosph., Sulfur, Silicon. Relat. Elem., 1996, vol. 99, p. 15.
Arsenyan, P., Oberte, K., Pudova, O., and Lukevics, E., Chem. Heterocycl. Comp., 2002, vol. 38, p. 1437.
Reid, D.H., Comp. Heterocyclic Chem., Oxford: Pergamon, 1996, vol. 4, p. 743.
Mugesh, R., Du Momt, W.-W., and Sies, U., Chem. Rev., 2001, vol. 101, p. 2125.
Saravanan, S., Amuthavalli, A., and Muthusubramanian, S., Indian J. Chem., 2009, vol. 48B, p. 1144.
Velikorodov, A.V., Imasheva, N.M., Kuanchalieva, A.K., and Poddubnyi, O.Yu., Russ. J. Org. Chem., 2010, vol. 46, p. 975.
Kuanchalieva, A.K., Cand. Sci. (Chem.) Dissertation, Astrakhan, 2011, p. 148.
Saravanan, S., Nithya, A., and Muthusubramanian, S., J. Heterocycl. Chem., 2006, vol. 43, p. 149.
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Original English Text © A.V. Velikorodov, V.A. Ionova, S.I. Temirbulatova, O.L. Titova, N.N. Stepkina, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1631–1637.
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Velikorodov, A.V., Ionova, V.A., Temirbulatova, S.I. et al. Synthesis and application of chalcones to the preparation of heterocyclic structures. Russ J Org Chem 49, 1610–1616 (2013). https://doi.org/10.1134/S1070428013110080
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DOI: https://doi.org/10.1134/S1070428013110080