Heterocyclic analogs of 5,12-naphthacenequinone 6. Synthesis of 4,11-dimethoxy derivatives of anthra-[2,3-<Emphasis Type="Italic">b</Emphasis>]thiophene-5,10-dione and anthra[2,3-<Emphasis Type="Italic">d</Emphasis>]isothiazole-5,10-dione |
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Authors: | A E Shchekotikhin Yu N Lusikov V N Buyanov M N Preobrazhenskaya |
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Institution: | (1) G. F. Gause Institute of New Antibiotics, Moscow, 119021, Russia;(2) D. Mendeleev University of Chemical Technology, Moscow, 125190 |
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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-dimethoxyanthra2,3-b]thiophene-5,10-dione-2-carboxylate and its 3-amino derivative respectively. Hydrolysis
of the ester group in methyl 4,11-dimethoxyanthra2,3-b]thiophene-5,10-dione-2-carboxylate and subsequent decarboxylation
of the carboxylic acid formed gave 4,11-dimethoxyanthra2,3-b]thiophene-5,10-dione. Condensation of 3-chloro-2-formyl-1,4-dimethoxyanthraquinone
with ammonia in the presence of sulfur gave 4,11-dimethoxyanthra2,3-d]isothiazole-5,10-dione
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538–543, April, 2007. |
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Keywords: | 3-chloro-1 4-dimethoxyanthracene-9 10-dione-2-carbaldehyde 4 11-imethoxyanthra[2 3-d]-isothiazole-5 10-dione 4 11-dimethoxyanthra[2 3-b]thiophene-5 10-dione derivatives fluorescence spectra Stokes shift |
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