Abstract
One-pot condensation of 4-hydroxycoumarin with arylglyoxals and ureas gave 4-aryl-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1H-imidazol-2(3H)-ones. The same compounds may be obtained from aroylbis(4-hydroxy-2-oxo-2H-chromen-3-yl)methanes and urea. The reaction of 4-bromobenzaldehyde with 4-hydroxycoumarin in the presence of urea led to the formation of the corresponding Michael adduct without participation of urea.
Similar content being viewed by others
References
Manolov, I., Maichle-Moessmer, C., and Danchev, N., Eur. J. Med. Chem., 2006, vol. 41, p. 882.
Manolov, I., Maichle-Moessmer, C., Nicolova, I., and Danchev, N., Arch. Pharm., 2006, vol. 336, p. 319.
Belikov, V.G., Farmatsevticheskaya khimiya (Pharmaceutical Chemistry), Moscow: Vysshaya Shkola, 1993.
Jackson, S.A., Sahni, S., Lee, L., Luo, Y., and Nieduzak, T.R., Bioorg. Med. Chem., 2005, vol. 13, p. 2723.
Choudhary, M., Fatima, N., Khan, K., Jalil, S., Iqbal, S., and Rahman, A., Bioorg. Med. Chem., 2006, vol. 14, p. 8066.
Sandeep, A., Devanand, B., and Shinde, R., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 6181.
Cravotto, G., Tagliapietra, S., Cappelo, R., Palmisano, G., Curini, M., and Boccalini, M., Arch. Pharm., 2006, vol. 336, p. 129.
Hamdi, M., Grech, O., Sakellariou, R., and Speziale, V., J. Heterocycl. Chem., 1994, vol. 31, p. 509.
Hamdi, N., Lidressi, C., Saoud, M., Nievas, A.R., and Zarrouk, H., J. Heterocycl. Chem., 2006, vol. 42, p. 36.
Burgart, Ya.V., Shcherbakov, K.V., Saloutin, V.I., and Chupakhin, O.N., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 1188.
Tonkina, N., Petrova, M., Belyakov, S., and Strakovs, A., Latv. Khim. Z., 2005, vol. 1, p. 51.
Kolos, N.N., Gozalishvili, L.L., Yaremenko, F.G., Shishkin, O.V., Shishkina, S.V., and Konovalova, I.S., Izv. Ross. Akad. Nauk, Ser. Khim., 2007, p. 2200.
Staunton, J., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 5. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1985, vol. 9, p. 62.
Kidwai, M., Saxena, S., and Mohan, R., Russ. J. Org. Chem., 2006, vol. 42, p. 52.
Balalaie, S., Soleiman-Beigi, M., and Rominger, F., J. Iran. Chem. Soc., 2005, vol. 2, p. 319.
Fisher, H.J., Ekeley, J.B., and Ronzio, A.R., J. Am. Chem. Soc., 1942, vol. 64, p. 1434.
Joshi, K.G., Pathal, V.N., and Goyal, M.K., J. Heterocycl. Chem., 1981, vol. 18, p. 1651.
Hough, T.L., Hough, I.R., and Pannell, R.W., J. Heterocycl. Chem., 1986, vol. 23, p. 1125.
Dabiri, M., Delbari, A.S., and Bazgir, A., Synlett, 2007, p. 821.
Liao, Y.X. and Kuo, P.Y., Tetrahedron Lett., 2003, vol. 44, p. 1599.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © N.N. Kolos, L.L. Gozalishvili, E.N. Sivokon’, I.V. Knyazeva, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 1, pp. 124–129.
Rights and permissions
About this article
Cite this article
Kolos, N.N., Gozalishvili, L.L., Sivokon’, E.N. et al. Reaction of 4-hydroxycoumarin with arylglyoxals and ureas. Russ J Org Chem 45, 119–125 (2009). https://doi.org/10.1134/S1070428009010151
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428009010151