Abstract
Oxidation of 5-hydroxy-6-methyluracil with molecular oxygen in the presence of copper(II) chloride involves formation of a 2 : 1 complex with copper(II). The rates of consumption of initial 5-hydroxy-6-methyluracil and oxygen were determined in the temperature range from 40 to 80°C. A probable reaction mechanism implies fixation and activation of molecular oxygen on the copper(II) complex with 5-hydroxy-6-methyluracil with formation of active oxygen species that are responsible for hydroxylation of the double C5=C6 bond in the uracil molecule.
Similar content being viewed by others
References
Hayatsu, H. and Iida, S., Tetrahedron Lett., 1969, vol. 10, no. 13, p. 1031.
Sevilla, M.D., Suryanarayana, D., and Morehouse, K.M., J. Phys. Chem., 1981, vol. 85, no. 8, p.1027.
Subbaraman, L.R., Subbaraman, J., and Behrman, E.J., J. Org. Chem., 1971, vol. 36, no. 9, p. 1256.
Matsui, M., Kamiya, K., Shibata, K., Muramarsu, H., and Nakazumi, H., J. Org. Chem., 1990, vol. 55, no. 4, p. 1396.
Knorre, D.G., Fedorova, O.S., and Frolova, E.I., Usp. Khim., 1993, vol. 62, no. 1, p. 70.
Al-Arab, M.M. and Hamilton, G.A., J. Am. Chem. Soc., 1986, vol. 108, no. 19, p. 5972.
Nugumanov, T.R., Ivanov, S.P., Starikova, Z.A., and Murinov, Yu.I., Mendeleev Commun., 2008, vol. 18, no. 4, p. 223.
Murinov, Yu.I., Nugumanov, T.R., Ivanov, S.P., Kletskii, M.E., Kamaletdinov, I.F., and Minkin, V.I., Khim. Geterotsikl. Soedin., 2009, vol. 45, no. 4, p. 586.
Zaripov, R.N., Safiullin, R.L., Rameev, Sh.R., Akhunov, I.R., and Komissarov, V.D., Kinet. Katal., 1990, vol. 31, no. 5, p. 1086.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © T.R. Nugumanov, A.V. Antipin, S.A. Grabovskii, N.N. Kabal’nova, Yu.I. Murinov, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 7, pp. 1195–1198.
Rights and permissions
About this article
Cite this article
Nugumanov, T.R., Antipin, A.V., Grabovskii, S.A. et al. Oxidation of 5-hydroxy-6-methyluracil with molecular oxygen in the presence of copper(II) chloride in aqueous solution. Russ J Gen Chem 81, 1543–1546 (2011). https://doi.org/10.1134/S107036321107022X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036321107022X