The alkylation of 3-(2-hydroxyethyl)-1H,3H-quinazoline-2,4-dione and subsequent bromination of its 1-allyl derivative have been studied. The data obtained has been compared with the results of similar studies on a series of other, related compounds. A rule has been formulated which allows a prediction of 1-allyl-substituted 2-oxo azaheterocycles bromination route based upon the way in which their initial alkylation by allyl bromide in the system DMSO–K2CO3 occurs.
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I. V. Ukrainets, E. V. Mospanova, L. V. Savchenkova, and S. I. Yankovich, Khim. Geterotsikl. Soedin., 90 (2011). [Chem. Heterocycl. Comp., 47, 67 (2011)].
I. V. Ukrainets, E. V. Mospanova, A. A. Davidenko, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1345 (2010). [Chem. Heterocycl. Comp., 46, 1084 (2010)].
I. V. Ukrainets, V. V. Kravtsova, A. A. Tkach, V. I. Mamchur, and E. Yu. Kovalenko, Khim. Geterotsikl. Soedin., 113 (2010). [Chem. Heterocycl. Comp., 46, 96 (2010)].
P. B. Terentev and A. P. Stankevicius, Mass Spectrometric Analysis of Biologically active Nitrogen Bases [in Russian], Mosklas, Vilnius (1987), p. 69.
J. -W. Chern, C.-Y. Shiau, and G.-Y. Lu, Bioorg. Med. Chem. Lett., 1, 571 (1991).
I. V. Ukrainets, N. L. Bereznyakova, O. V. Gorokhova, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1546 (2009). [Chem. Heterocycl. Comp., 45, 1241 (2009)].
A. F. Pozharskii, Theoretical Bases of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985), p. 158.
M. V. Slivka, Thesis Cand. Chem. Sci., Kiev (2001).
M. V. Slivka, S. M. Khripak, V. N. Britsun, and V. I. Staninets, Zh. Org. Khim., 36, 1064 (2000).
S. M. Khripak, M. V. Slivka, R. V. Vilkov, R. N. Usenko, and V. G. Lendel, Khim. Geterotsikl. Soedin., 922 (2007). [Chem. Heterocycl. Comp., 43, 781 (2007)].
R. F. Elderfield (editor), Heterocyclic Compounds [Russian translation], Vol. 6, Inostr. Lit., Moscow (1960), p. 289.
J. M. Domagala, E. L. Ellsworth, L. Huang, T. E. Renau, R. Singh, and M. A. Stier, US Pat. 6331538 (2001).
M. Sui, EP Pat. 1708713 (2005).
P. Bird, E. L. Ellsworth, D. Q. Nguyen, J. P. Sanchez, H. D. H. Showalter, R. Singh, M. A. Stier, T. P. Tran, B. M. Watson, and J. Yip, US Pat. 7094780 (2006).
C. Vigne, M. Buti, C. Montginoul, E. Torreilles, and L. Giral, J. Heterocycl. Chem., 13, 921 (1976).
M. Susse and S. Johne, Monatsh. Chem., 118, 71 (1987).
M. Khalifa, A. N. Osman, M. G. Ibrahim, A.-R. E. Ossman, and M. A. Ismail, Pharmazie, 37, 115 (1982).
A. Rivero, L. Guerrero, K. A. Espinoza, M. C. Meza, and J. R. Rodriguez, Molecules, 14, 1860 (2009).
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For Communication 195, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 885–891, June, 2011.
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Ukrainets, I.V., Mospanova, E.V., Turov, A.V. et al. 4-hydroxy-2-quinolones 196. synthesis and bromination of 1-allyl-3-(2-hydroxyethyl)-1h,3h-quinazoline-2,4-dione. Chem Heterocycl Comp 47, 731–736 (2011). https://doi.org/10.1007/s10593-011-0827-8
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DOI: https://doi.org/10.1007/s10593-011-0827-8