| 5-取代吲哚-2-酮的合成 |
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| 引用本文： | 李占成,金云舟,高博.5-取代吲哚-2-酮的合成[J].合成化学,2012,20(1):119-122. |
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| 作者姓名： | 李占成 金云舟 高博 |
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| 作者单位： | 1. 同济大学,上海,200092
2. 同济大学生命科学与技术学院,上海,200092 |
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| 摘 要： | 4-取代苯胺依次与水合氯醛及盐酸羟胺反应制得4-取代异亚硝基乙酰苯胺(2a～2e);2在浓硫酸作用下环合制得5-取代靛红(3a～3e);3通过改进的Wolff-Kishner-黄鸣龙反应合成了重要的药物中间体——5-取代吲哚-2-酮(5a～5e);5a通过硝化制得5-硝基吲哚-2-酮(5f);5f被还原制得5-氨基吲哚-2-酮(5g)。其结构经1H NMR和MS确证。
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| 关 键 词： | 5-取代吲哚-2-酮 Wolff-Kishner-黄鸣龙反应 药物中间体 合成 |
Synthesis of 5-Substituted Indol-2-ones |
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| LI Zhan-cheng
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JIN Yun-zhou
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GAO Bo.Synthesis of 5-Substituted Indol-2-ones[J].Chinese Journal of Synthetic Chemistry,2012,20(1):119-122. |
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| Authors: | LI Zhan-cheng JIN Yun-zhou GAO Bo |
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| Institution: | 1b(a.Department of Chemistry,b.School of Life Sciences and Technology, 1.Tongji University,Shanghai 200092,China) |
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| Abstract: | 4-Substituted isonitroacetanilines(2a~2e) were prepared by the reaction of 4-substituted anilines with chloral hydrate and hydroxylamine hydrochloride.5-Substituted isatins(3a~3e) were prepared by the cyclization of 2 in the presence of concentrated sulfuric acid.The key drug intermediates,5-substituted indol-2-ones(5a~5e),were synthesized from 3 by a improved Wolff-Kishner-Huang reduction.5a was nitrified to obtain 5-nitryl-indol-2-ones(5g),then reduced to give 5-amido-indol-2-ones(5f).The structures were confirmed by 1H NMR and MS. |
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| Keywords: | 5-substituted indol-2-one Wolff-Kishner-Huang reduction drug intermediate synthesis |
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