Abstract
4-Halo-1-aminoanthraquinones are formed when anthra [1,9-cd]isoxazol-6-ones are refluxed in hydrohalic acids. The 3 position undergoes halogenation when 5-substituted isoxazoles are used. The process takes place via a one-proton mechanism with the participation of halide ion in the rate-determining step, possibly with the intermediate formation of N-haloaminoanthraquinones.
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A. Schaarschmidt, Ber., 49, 1635 (1916).
K. K. Mozgova, Zh. Obshch. Khim., 19, 773 (1949).
H. Labhart, Helv. Chim. Acta, 40, 1410 (1957).
S. Mori, A. Inoue, N. Kuroki, and K. Konishi, J. Soc. Org. Synth. Chem., Jpn., 23, 259 (1965).
K. Fries and F. Schumann, Chem. Ber., 52, 2192 (1919).
L. N. Nikolenko, Laboratory Manual of Intermediates and Dyes [in Russian], 2nd edn., Moscow (1965), p. 41.
N. S. Dokunikhin and L. V. Galitsyna, Dokl. Akad. Nauk SSSR, 179, 1099 (1968).
N. M. Émanuél' and D. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1974), p. 274.
A. Gordon and R. Ford, The Chemist's Companion, Wiley (1973).
M. I. Vinnik, R. N. Kruglov, and N. M. Chirkov, Zh. Fiz. Khim., 30, 827 (1956).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1471–1473, November, 1980.
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Gornostaev, L.M., Sakilidi, V.T. Transformations of anthra[1,9-cd]isoxazol-6-ones in hydrohalic acids. Chem Heterocycl Compd 16, 1112–1114 (1980). https://doi.org/10.1007/BF00504104
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DOI: https://doi.org/10.1007/BF00504104