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Studies on quinones

VI. Reaction of anthra[1,2-c]-1,2,5-thiadiazole-6,11-dione with nucleophilic agents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In the reaction of anthra[1, 2-c]-1, 2,-5-thiadiazole-6,11-dione (I) with mercaptans, atylsulfinic acids, and bisulfite, the nucleophilic agent is directed into position 4 of the nucleus with the formation of substituted hydroquinones, the oxidation of which leads, respectively, to 4-aryl(alkyl)thio, 4-arylsulfonyl, and 4-sulfo derivatives of anthra [1,2-c]-1,2,5-thiadiazole-6,11-dione (II, VI, IX). When entry into position 4 is impossible, addition to the carbonyl oxygen atom takes place. On being heated with bisulfite, the quinonesulfonic acid IX is converted into the monsulfuric acid ester of the hydroquinonesulfonic acid X, and on reaction with benzenesulfinic acid 4-phenylsulfonylanthraquinonethiadiazole (VIa) is converted into the benzenesulfonic acid monoester XI.

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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 & S. B. Lantsman

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  1. M. V. Gorelik
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  2. S. B. Lantsman
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Additional information

For part V, see [1].

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Gorelik, M.V., Lantsman, S.B. Studies on quinones. Chem Heterocycl Compd 4, 337–341 (1968). https://doi.org/10.1007/BF00755275

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  • DOI: https://doi.org/10.1007/BF00755275

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