Synthesis of thiopheno-quinizarine derivatives |
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Authors: | Yu B Sinkevich A E Shchekotikhin Yu N Luzikov V N Buyanov L V Kovalenko |
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Institution: | (1) D. I. Mendeleev University of Chemical Technology of Russia, Moscow, 125047;(2) G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Science, Moscow, 119021, Russia |
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Abstract: | 4,11-Dihydroxyanthra2,3-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-dibutoxyanthra2,3-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-methylanthra2,3-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-anthra2,3-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-anthra2,3-b]thiophene-5,10-diones.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1478–1485, October, 2007. |
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Keywords: | 4 11-dihydroxyanthra[2 3-b]thiophene-5 10-dione 4 11-dimethoxy-3-methylanthra[2 3-b]-thiophene-5 10-dione 2-mercaptoquinizarine alkylation hydrolysis radical bromination cyclization |
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