Heterocyclic analogs of 5,12-naphthacenequinone 15. Synthesis of new anthra[2,3-b]thiophene-3(2)-carboxylic acids

Methods have been developed for the synthesis of anthra[2,3- b ]thiophene-3(2)-carboxylic acids and their derivatives through modifications of 4,11-dibutoxy-3-methylanthra[2,3- b ]thiophene-5,10-dione. A scheme involving methyl group transformations was proposed for the preparation of dibutoxyanthra...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-06, Vol.54 (6), p.612-617
Main Authors: Andreeva, Daria V., Sinkevich, Yuri B., Tikhomirov, Alexander S., Luzikov, Yury N., Korolev, Alexander M., Shchekotikhin, Andrey E.
Format: Article
Language:English
Subjects:
Carboxylic acids
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemotherapy
Halogenation
Heterocyclic compounds
Hydrolysis
Organic acids
Organic Chemistry
Oxidation
Pharmacy
Thiophene
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Summary:Methods have been developed for the synthesis of anthra[2,3- b ]thiophene-3(2)-carboxylic acids and their derivatives through modifications of 4,11-dibutoxy-3-methylanthra[2,3- b ]thiophene-5,10-dione. A scheme involving methyl group transformations was proposed for the preparation of dibutoxyanthra[2,3- b ]thiophene-3-carboxylic acid, including reactions of radical halogenation, hydrolysis, and oxidation of a 3-formyl derivative. 4,11-Dihydroxy-3-methylanthra[2,3- b ]thiophene-2-carboxylic acid was synthesized from the appropriate carbonitrile, obtained by Rosenmund–von Braun reaction from 2-bromo-4,11-dibutoxy-3-methylanthra[2,3- b ]-thiophene-5,10-dione.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-018-2316-9