Multi-bromination of 1,8-dihydroxy-9- anthrone, important intermediates in the synthesis of antipsoriatic drugs
نویسنده
چکیده
10-bromo-1,8-dihydroxy-9-anthrone (10-bromoanthralin) was synthesized with precise ratio of bromine to anthralin (1.10:1), respectively. With this ratio of the reagents, the reaction is repetitive at any scale. This compound is a highly significant intermediate for the synthesis of many anthralin derivetised antipsoriatic drugs. Bromination at both benzylic and aromatic ring positions of anthralin was achieved without using any conventional Lewis acid catalyst. Also, multibromination of aromatic rings of anthralin was achieved exclusively in acetic acid and acetic acid/chloroform solvent.
منابع مشابه
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Anthralin and some of its derivatives have implied antipsoriatic effect in clinical and pharmaceutical studies. Anthralin is synthesized by different strategies. In this work we report the synthesis of "OEHA" as a precursor of another biological active compound.
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The synthetic route in this work is based on the classical Friedel-Crafts strategy, and began with 1,4-dimethoxybenzene (I), followed by alkylation and selective demethylation of 2-methoxy function in 0x0-acid (3). The orthoformylation to synthesize aldehyde (6) was based on the Reimer-Tieman reaction. Chain extension of this aldehyde required methylation of the hydroxyl group and condensat...
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Treatment of 5,8-dihydroxy-1-tetralone (9) with either 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in refluxing benzene or silver (I) oxide in refluxing 1,4-dioxane afforded juglone (5-hydroxy-1,4-naphthoquinone) (1) in good yield. With manganese dioxide in dioxane the tetralone gave a mixture of juglone and naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) (3), the proportion of naphthazarin...
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تاریخ انتشار 2003