SYNTHESIS OF THIOPHENOQUINIZARINE DERIVATIVES

Authors

  • Ю. Б. Синкевич D. I. Mendeleev University of Chemical Technology of Russia, Moscow 125047
  • А. Е. Щекотихин D. I. Mendeleev University of Chemical Technology of Russia, Moscow 125047 G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Science, Moscow 119021
  • Ю. H. Лузиков G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Science, Moscow 119021
  • В. Н. Буянов D. I. Mendeleev University of Chemical Technology of Russia, Moscow 125047
  • Л. В. Коваленко D. I. Mendeleev University of Chemical Technology of Russia, Moscow 125047

DOI:

https://doi.org/10.1007/7365

Keywords:

4, 11-dihydroxyanthra[2, 3-b]thiophene-5, 10-dione, 11-dimethoxy-3-methylanthra[2, 2-mercaptoquinizarine, alkylation, hydrolysis, radical bromination, cyclization

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.

How to Cite
Sinkevich, Yu. B.; Shchekotikhin, A. E.; Luzikov, Yu. N.; Buyanov, V. N.; Kovalenko, L. V.  Chem. Heterocycl. Compd. 2007, 43, 1252. [Khim. Geterotsikl. Soedin. 2007, 1478.]

For this article in the English edition see DOI 10.1007/s10593-007-0191-x

 

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Published

2023-01-24

Issue

No. 10 (2007)

Section

Original Papers