Abstract
Naphtho[2,3-f]quinoxaline-7,12-diones add a molecule of benzenesulfinic acid to give 5-phenylsulfonyl-7, 12-dihydroxynaphtho[2,3-f]quinoxalines. The latter are oxidized to 5-phenylsulfonyl-substituted quinones, which add a molecule of benzenesulfinic acid to the oxygen atoms of the quinone grouping to give the O7-benzenesulfonate of 5-phenylsulfonyl-7, 12-dihydroxynaphtho[2,3-f]quinoxaline. The protonated form of naphtho[2,3-f]quinoxa-line-7, 12-dione, which is stabilized by an intramolecular hydrogen bond, as confirmed by the anomalously high basicity of angular naphtho[2,3-f]quinoxaline-7,12-dione as compared with its linear isomer, which is inert in reactions with benzenesulfinic acid, undergoes reaction.
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See [1] for communication XXVII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1271–1274, September, 1974.
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Gorelik, M.V., Bazrukova, T.F. Investigation of quinones. Chem Heterocycl Compd 10, 1105–1108 (1974). https://doi.org/10.1007/BF00472136
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DOI: https://doi.org/10.1007/BF00472136