Abstract
The cyclization of 2-nitroso-4-nitropropiophenone under the influence of hydrogen chloride proceeds in a more complex manner than in the cases previously described for other 4-substituted-2-nitrosopropiophenones: three, rather than two, haloanthranils are formed, and their formation is accompanied simultaneously by a number of redox transformations. This fact is explained by a decrease in the ability of the carbonyl group in the investigated ketone to undergo protonation.
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Yu. S. Shabarov, S. S. Mochalov, A. N. Fedotov, and V. V. Kalashnikov, Khim. Geterotsikl. Soedin., No. 9, 1195 (1975).
Yu. S. Shabarov and S. S. Mochalov, Khim. Geterotsikl. Soedin., No. 10, 1334 (1973).
S. S. Mochalov, T. P. Surikova, and Yu. S. Shabarov, Khim. Geterotsikl. Soedin., No. 7, 886 (1976).
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Yu. S. Shabarov, S. S. Mochalov, and O. M. Khryashchevskaya, Zh. Org. Khim.,6, 2434 (1970).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1334–1337, October, 1976.
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Mochalov, S.S., Surikova, T.P. & Shabarov, Y.S. Behavior of 2-nitroso-4-nitropropiophenone under conditions of cyclization to haloanthranils. Chem Heterocycl Compd 12, 1106–1109 (1976). https://doi.org/10.1007/BF00945589
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DOI: https://doi.org/10.1007/BF00945589