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化学学报
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化学学报 ›› 1982, Vol. 40 ›› Issue (4): 359-361. 上一篇    下一篇

研究简报

三甲氧基蒽醌的新合成法

张椿年, 徐卓君, 郑春雷   

  1. 上海医药工业研究院
  • 投稿日期:1979-09-14 发布日期:2013-06-03
  • 通讯作者: 张椿年

A NEW METHOD FOR THE SYNTHESIS OF 1, 4, 5-TRIMETHOXYANTHRAQUINONE

ZHANG CHUN-NIEN, XU ZHUO-JUN, ZHENG CHUN-LEI   

  1. Shanghai Institute of Pharmaceutical Industrial Research
  • Received:1979-09-14 Published:2013-06-03

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3

阿霉素(1)是目前常用的广谱抗肿瘤药物,其全合成研究引起了广泛的注意。Kende等[1]曾自1,4,5-三甲氧基蒽醌(2)成功地合成了它的配基阿霉酮.三甲氧基蒽醌的合成,早期系以1,4,5-三氯蒽醌与甲醇钠加压反应制成[2],但不易获得纯三氯蒽醌.Kende等系以3-甲氧基邻苯二甲酸酐与1,4-二甲氧基苯经Friedel-Crafts反应制得.最近Baldwin和Bair[3]以间甲氧基苯甲酰苯胺,通过邻位金属化,经七步反应制得类似的1-羟基-4,5-二甲氧基蒽醌(3).

A reaction sequence for the preparation of the anthraoyclinone precursor,1,4,5,-trimethogyanthraquinone (2),was described.Thus,quinizarin (4) was chlorinated with thionyl chloride to give 10-ohloro-l-hydrozy-anthraquinone-[4,9] (6).Nitration of 5 followed by hydrolysis,5-nitroquinizarin (6) was obtained in good yield and high purity.Methylation of the nitroquinizarin with dimethyl snlfatepotassium carbonate in butanone afforded5-nitro-1,4-dimethogyanthraqninone (7).The trimethozyanthraquinone (2) was then obtained by subsequent nucleophilio substitution using sodium methozide in methanol.