Abstract
The photochemical reactions of 4-methyl-7-diethylaminocoumarin with a series of alkyl halides including isopropyl iodide, allyl iodide, bromoacetone α-bromoethyl acetate, phenacyl bromide, p-bromophenacyl bromide, and chloroacetonitrile, and aryl iodides including iodobenzene, 2-nitroiodobenzene, 3,4-dimethoxyiodobenzene, and 3-iodo-4-methyl-7-diethylaminocoumarin proceed by a radical addition mechanism to give 3-substituted aminocoumarins. A series of 3-substituted 7-aminocoumarins was also obtained as a result of the photochemical reactions of 4-methyl-7-diethylaminocoumarin, with other reagents, having photolabile chemical bonds such as dioxanyl peroxide, phenyl iodosodiacetate, and nitromethane. The luminescence characteristics of the compounds synthesized were studied.
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Literature Cited
M. A. Kirpichenok, L. M. Mel'nikova, L. K. Denisov, I. I. Grandberg, and N. P. Akimova, Khim. Geterotsikl. Soedin., No. 1, 30 (1989).
M. A. Kirpichenok, L. M. Mel'nikova, L. K. Denisov, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 9, 1169 (1988).
M. A. Kirpichenok, L. M. Mel'nikova, D. S. Yufit, Yu. T. Struchkov, I. I. Grandberg, and L. K. Denisov, Khim. Geterotsikl. Soedin., No. 9, 1176 (1988).
D. Dopp and J. Heufer, J. Photochem., 32, 243 (1986).
G. Jones, W. R. Bergmark, and W. R. Jackson, Opt. Commun., 50, 320 (1984).
R. J. Trebra and T. H. Koch, Appl. Phys. Lett., 42, 129 (1983).
P. J. Kropp, G. S. Poindexter, N. J. Pienta, and D. C. Hamilton, J. Am. Chem. Soc., 98, 8135 (1976).
M. A. Kirpichenok, I. I. Grandberg, L. K. Denisov, and L. M. Mel'nikov, Izv. TSKhA, No. 3, 172 (1985).
R. S. Davidson, J. W. Goodin, and G. Kemp, Adv. Phys. Org. Chem., 20, 191 (1984).
P. J. Kropp, Acc. Chem. Res., 17, 131 (1984).
G. Jones, W. R. Jackson, C. Choi, and W. R. Bergmark, J. Org. Chem., 49, 2705 (1984).
G. O. Becker, Introduction to Organic Photochemistry [Russian translation], Izd. Khimiya, Leningrad (1976).
I. I. Grandberg, L. K. Denisov, and O. A. Popova, Khim. Geterotsikl. Soedin., No. 2, 147 (1987).
M. Julliard and M. Chanon, Chem. Rev., 83, 425 (1983).
N. J. Bunce, P. Pilon, L. O. Ruzo, and D. J. Sturch, J. Org. Chem., 41, 3023 (1976).
J. A. Barltrop and J. Coyle, Excited States in Organic Chemistry [Russian translation], Izd. Mir, Moscow (1978).
S. Parker, Solution Photoluminescence [Russian translation], Izd. Mir, Moscow (1972).
M. A. Kirpichenok, S. L. Levchenko, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 10, 1324 (1987).
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For Communication 3, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 460–469, April, 1989.
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Kirpichenok, M.A., Mel'nikova, L.M., Denisov, L.K. et al. Photochemical reactions of 7-aminocoumarins. 4. Reaction of 4-methyl-7-diethylaminocoumarin with compounds tending to photolytic dissociation. Chem Heterocycl Compd 25, 380–388 (1989). https://doi.org/10.1007/BF00480748
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DOI: https://doi.org/10.1007/BF00480748