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Synthesis of thiopheno-quinizarine derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4,11-Dihydroxyanthra[2,3-b]thiophene-5,10-dione (thiophenoquinizarine) and its 3-methyl derivative were obtained by the cyclization of quinizarin-2-yl derivatives of mercaptoacetaldehyde or mercaptoacetone in acid medium. 4,11-Dimethoxy-and 4,11-dibutoxyanthra[2,3-b]thiophene-5,10-dione were synthesized by the alkylation of the hydroxyl group in the synthesized anthrathiophenes with dimethylformamide dimethylacetal or butyl iodide respectively. Radical bromination of 4,11-dimethoxy-3-methylanthra[2,3-b]thiophene-5,10-dione, depending on the amount of N-bromo-succinimide taken, leads to the formation of 3-bromomethyl-or 3-dibromomethyl-4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-diones. The action of sodium acetate on the obtained bromo derivatives with subsequent hydrolysis of the intermediate acetates led to the synthesis of 3-hydroxymethyl-or 3-formyl-4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-diones.

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Authors and Affiliations

  1. D. I. Mendeleev University of Chemical Technology of Russia, Moscow, 125047

    Yu. B. Sinkevich, A. E. Shchekotikhin, V. N. Buyanov & L. V. Kovalenko

  2. G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Science, Moscow, 119021, Russia

    A. E. Shchekotikhin & Yu. N. Luzikov

Authors
  1. Yu. B. Sinkevich
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  2. A. E. Shchekotikhin
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  3. Yu. N. Luzikov
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  4. V. N. Buyanov
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  5. L. V. Kovalenko
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Correspondence to Yu. B. Sinkevich.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1478–1485, October, 2007.

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Sinkevich, Y.B., Shchekotikhin, A.E., Luzikov, Y.N. et al. Synthesis of thiopheno-quinizarine derivatives. Chem Heterocycl Comp 43, 1252–1259 (2007). https://doi.org/10.1007/s10593-007-0191-x

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  • DOI: https://doi.org/10.1007/s10593-007-0191-x

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