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Formation of 4,7-dioxo-5-acetamido-4,7-dihydrobenzofurazan from 4-oxo-5-hydroximino-4,5,6,7-tetrahydrobenzofurazan and -furoxan and investigation of its reaction with amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 4-oxo-5-hydroximino-4,5,6,7-tetrahydrobenzofurazan and 4-oxo-5-hydroximino-4,5,6,7-tetrahydrobenzofuroxan with acetic anhydride in the presence of an acid gives 4,7-diacetoxy-5-acetamidobenzofurazan and 2,3-diacetoximino-5-acetamido-1,4-benzoquinone, respectively, which were used to obtain 4,7-dioxo-5-acetamido-4,7-dihydrobenzofurazan. The synthesized quinone reacts with amines to give the corresponding aminoquinones; when 4,7-dioxo-5-acetamido-6-anilino-4,7-dihydrobenzofurazan is heated, it is readily converted to 5-phenyl-6-methyl-4,8-dioxo-1H-imidazo[4,5-f]benzofurazan.

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References

  1. V. A. Samsonov and L. B. Volodarskii, Khim. Geterotsikl. Soedin., No. 10, 1408 (1991).

    Google Scholar 

  2. N. N. Vorozhtsov and V. A. Koptyug, Zh. Obshch. Khim., 28, 1646 (1958).

    Google Scholar 

  3. J. F. W. McOmic and J. M. Blatcly, “The Thiele—Winter acetoxylation of quinones,” Organic Reactions, Vol. 19, John Wiley and Sons, Inc., New York—Sydney—Toronto (1972), p. 199.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 532–536, April, 1993.

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Samsonov, V.A., Volodarskii, L.B. Formation of 4,7-dioxo-5-acetamido-4,7-dihydrobenzofurazan from 4-oxo-5-hydroximino-4,5,6,7-tetrahydrobenzofurazan and -furoxan and investigation of its reaction with amines. Chem Heterocycl Compd 29, 455–459 (1993). https://doi.org/10.1007/BF00529887

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  • DOI: https://doi.org/10.1007/BF00529887

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