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Heterocyclic analogs of 5,12-naphthacenequinone 6. Synthesis of 4,11-dimethoxy derivatives of anthra-[2,3-b]thiophene-5,10-dione and anthra[2,3-d]isothiazole-5,10-dione

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Abstract

Condensation of 2-formyl-or 2-cyano-3-chloro-1,4-dimethoxyanthraquinone with methyl thioglycolate in the presence of base gave methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and its 3-amino derivative respectively. Hydrolysis of the ester group in methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and subsequent decarboxylation of the carboxylic acid formed gave 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione. Condensation of 3-chloro-2-formyl-1,4-dimethoxyanthraquinone with ammonia in the presence of sulfur gave 4,11-dimethoxyanthra[2,3-d]isothiazole-5,10-dione

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Authors and Affiliations

  1. G. F. Gause Institute of New Antibiotics, Moscow, 119021, Russia

    A. E. Shchekotikhin, Yu. N. Lusikov & M. N. Preobrazhenskaya

  2. D. Mendeleev University of Chemical Technology, Moscow, 125190

    V. N. Buyanov

Authors
  1. A. E. Shchekotikhin
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  2. Yu. N. Lusikov
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  3. V. N. Buyanov
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  4. M. N. Preobrazhenskaya
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538–543, April, 2007.

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Shchekotikhin, A.E., Lusikov, Y.N., Buyanov, V.N. et al. Heterocyclic analogs of 5,12-naphthacenequinone 6. Synthesis of 4,11-dimethoxy derivatives of anthra-[2,3-b]thiophene-5,10-dione and anthra[2,3-d]isothiazole-5,10-dione. Chem Heterocycl Compd 43, 439–444 (2007). https://doi.org/10.1007/s10593-007-0063-4

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  • DOI: https://doi.org/10.1007/s10593-007-0063-4

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