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Studies on quinones

VIII. Addition reactions to anthraquinonefurazans

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Anthra[1,2-c][1,2,5]oxadiazole-6,11-dione (I) was added to benzenesulfinic acid and thiophenol with the formation of 4-phenyl-sulfonyl- and 4-phenylmercapto-substituted hydroquinones, which on oxidation were converted into the corresponding quinones III and VII. 4-Phenylsulfonylanthra[1,2-c][1,2,5]oxadiazole-6,11-dione (III), in turn, reacted readily with benzenesulfinic acid, adding a molecule of the latter to the carbonyl oxygen atom and was converted into the O-benzenesulfonic monoester [6] (IV). Using compounds IV and hydroxynaphtho[1,2-c][1,2,5]oxadiazole (XId) the capability of the nitrogen atom of the furazan ring of participating in the formation of intramolecular hydrogen bonds was shown.

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References

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Authors and Affiliations

  1. Scientific-Research Institute for Organic Intermediates and Dyes, Moscow

    M. V. Gorelik, B. E. Zaitsev, T. P. Kononova & N. S. Dokunikhin

Authors
  1. M. V. Gorelik
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  2. B. E. Zaitsev
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  3. T. P. Kononova
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  4. N. S. Dokunikhin
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Additional information

For part VII, see [1].

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Gorelik, M.V., Zaitsev, B.E., Kononova, T.P. et al. Studies on quinones. Chem Heterocycl Compd 4, 566–568 (1971). https://doi.org/10.1007/BF00481016

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  • DOI: https://doi.org/10.1007/BF00481016

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