Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Oxytetracycline and Related Compounds. XVIII. Syntheses of 1-Hydroxy-3, 10-dimethylanthrone and 6-Hydroxy-12-methyl-5(12H)-naphthacenone.
堀井 善一森川 浩一成瀬 正織田村 恭光
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1963 年 11 巻 2 号 p. 152-155

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The Grignard reaction of 1-hydroxy-3-methylanthraquinone (II) with methylmagnesium iodide yielded 1, 10-dihydroxy-3, 10-dimethylanthrone (III), which was converted to 3, 10-dimethyl-1-hydroxyanthrone (VI) by reduction with hydriodic acid. Compound VI was also obtained by hydrolysis with hydrochloric acid of 1, 9-diacetoxy-3, 10-dimethyl-anthracene (V), which was prepared by reductive acetylation of III with zinc dust, sodium acetate and acetic anhydride. The method was also found to be applicable to 6-hydroxy-5, 12-naphthacenequinone (IX), thus giving 6-hydroxy-12-methyl-5 (12H)-naphthacenone (XI).
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© The Pharmaceutical Society of Japan
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