Abstract
The reactions of substituted coumarins with a variety of halogenating agents, leading to the formation of the corresponding 3-chloro-, 3-bromo-, and 3-iodo-7-aminocoumarins, have been studied. It has also been shown, based on the results of studies of the spectral-luminescence and acid-base characteristics of these 3-halo-7-aminocoumarins, that their basicity increases as the electron-donating nature of the substituent in the 4-position increases, and is also greater, as expected, for 3-iodo- and 3-chloro derivatives than for 3-bromo derivatives.
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Literature Cited
M. A. KirpichËnok, S. L. Levchenko, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 10, 1324 (1987).
N. A. Gordeeva, M. A. KirpichËnok, D. S. Yufit, Yu. T. Struchkov, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 8, 1033 (1990).
N. A. Gordeeva, M. A. KirpichËnok, A. I. Chernyshev, I. I. Grandberg, and N. P. Akimova, Khim. Geterotsikl. Soedin., No. 9, 1172 (1990).
N. A. Gordeeva, M. A. KirpichËnok, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 11, 1469 (1990).
M. A. KirpichËnok, S. K. Gorozhankin, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 7, 888 (1989).
M. A. KirpichËnok, S. K. Gorozhankin, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 6, 836 (1990).
M. A. KirpichËnok, I. I. Grandberg, L. K. Denisov, and L. M. Mel'nikova, Izv. Timir. Sel'skho-khoz. Akad., No. 3, 172 (1985).
L. A. Karandashova, N. S. Patalakha, P. B. Kurapav, M. A. KirpichËnok, S. K. Gorozhankin, I. I. Grandberg, and L. K. Denisov, Izv. Timir. Sel'sko-khoz. Akad., No. 1, 188 (1988).
S. K. Gorozhankin, M. A. KirpichËnok, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 10, 1326 (1990).
S. Parker, Photoluminescence of Solutions [Russian translation], Mir, Moscow (1972), p. 510.
G. Jones, W. R. Jackson, Ch.-yoo Choi, and W. R. Bergmark, J. Phys. Chem., 89, 294 (1985).
L. A. Karandashova, M. A. KirpichËnok, D. S. Yufit, Yu. T. Struchkov, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 12, 1610 (1990).
M. Maroncelli and G. R. Fleming, J. Phys. Chem., 86, 6221 (1987).
M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, and R. W. Taft, J. Org. Chem., 48, 2877 (1983).
M. J. Kamlet, C. Dickinson, and R. W. Taft, Chem. Phys. Lett., 77, 69 (1981).
P. R. Wells, S. Ehrensons, and R. W. Taft, Progr. Phys. Org. Chem., 6, 147 (1968).
R. W. Taft and C. A. Grob, J. Am. Chem. Soc., 96, 1236 (1874).
H. Duddeck and M. Kaiser, Org. Magn. Reson., 20, 55 (1982).
J. Demas and G. A. Crosby, J. Phys. Chem., 75, 1010 (1971).
I. Y. Berstein and U. L. Kaminsky, Spectrophotometric Analysis in Organic Chemistry [Russian translation], Khimiya, Leningrad (1986), p. 200.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1600–1609, December, 1990.
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Gordeeva, N.A., KirpichËnok, M.A., Patalakha, N.S. et al. Synthesis, spectral-luminescence, and acid-base properties of 3-halo-7-aminocoumarins. Chem Heterocycl Compd 26, 1329–1337 (1990). https://doi.org/10.1007/BF00473959
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DOI: https://doi.org/10.1007/BF00473959