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6-甲氧基靛红的合成工艺改进

王鸿玉,  宋云龙,  章玲,  曾强,  朱驹,  张辉

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文章导航 > 药学实践与服务  > 2015 >  33(2): 127-130
王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
引用本文: 王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
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WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
Citation: WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
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6-甲氧基靛红的合成工艺改进

doi: 10.3969/j.issn.1006-0111.2015.02.009
  • 1.

    沈阳药科大学制药工程学院, 辽宁 沈阳 110016;第二军医大学药学院药物化学教研室, 上海 200433

  • 2.

    第二军医大学药学院药物化学教研室, 上海 200433

  • 3.

    沈阳药科大学制药工程学院, 辽宁 沈阳 110016

基金项目: 国家自然科学基金项目(81172928,21102174)

Improvement of synthesis method of 6-methoxyisatin

  • 1.

    School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China;Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

  • 2.

    Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

  • 3.

    School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China

  • 摘要: 目的 探索6-甲氧基靛红的合成工艺改进方法。 方法 以3-甲氧基苯胺为起始原料,经Sandmeyer方法首先生成中间体1-肟基-N-(3-甲氧基苯基)乙酰胺,在甲磺酸催化下关环得到6-甲氧基靛红。 结果 在关环反应中,催化剂采用甲磺酸,替代文献中常用的浓硫酸,温度80℃,反应30 min,收率达81.24%。 结论 提出了一条操作简单、条件温和、收率高的6-甲氧基靛红的合成工艺,适合大量制备。
    Abstract: Objective To improve the synthetic condition of 6-methoxyisatin. Methods The starting material 3-methoxyaniline was firstly converted into the intermediate 1-oximino-N- (3-methoxyphenyl) acetamide through Sandmeyer reaction, then 6-methoxyisatin was conducted with methanesulfonic acid as catalyst in the following ring closure reaction. Results In the second step of the cyclization reaction, methanesulfonic acid was used to replace the concentrated sulfuric acid which is widely used in literature. The temperature was 80℃, the reaction time was 30 min, and the yield was 81.24%. Conclusion This study provided a synthesis process of 6-methoxyisatin with simple operation, mild reaction condition and high yield, which is suitable for large scale preparation of the compound.
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    [4] Lerchner A, Carreira EM. First total synthesis of (+/-)-strychnofoline via a highly selective ring-expansion reaction[J]. J Ame Chem Soc,2002, 124(50): 14826-14827.
    [5] Petrov RR, Ferrini ME, Jaffar Z, et al. Design and evaluation of a novel fluorescent CB2 ligand as probe for receptor visualization in immune cells[J]. Bioorg Med Chem Lett, 2011, 21(19): 5859-5862.
    [6] Jag M, Virender S. Condensed bridgehead nitrogen heterocyclic systems: synthesis and antimicrobial activity of thiazolo[3', 2':2,3][1,2,4]triazino[5,6-b]indoles and isomeric thiazolo[2',3':3,4][1,2,4]triazino[5,6-b]indoles[J]. Ind J Chem, Sec B: Org Chem Includ Medicin Chem, 1996, 35(5): 456-458.
    [7] Kaila N, Janz K, DeBernardo S, et al. Synthesis and abiological evaluation of quinoline salicylic acids as P-selectin antagonists[J]. J Medicin Chem, 2007, 50(1): 21-39.
    [8] 张晓飞, 刘华业, 高文涛. 取代靛红改进方法的合成[J]. 渤海大学学报(自然科学版), 2009, 33(3): 212-216.
    [9] Mason JJ, Janosik T, Bergman J. A new approach to methoxyisatins leading to the total synthesis of ophiuroidine and other hydroxytryptanthrins[J]. Synthesis-Stuttgart, 2009, (21): 3642-3648.
    [10] Soderberg BCG, Gorugantula SP, Howerton CR, et al. A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes[J]. Tetrhedron, 2009, 65(36):7357-7363.
    [11] Parsy CC,Surleraux D,Alexandre FR,et al.Macrocyclic serine protease inhibitors[P].美国,2009099596,2009-08-13.
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出版历程
  • 收稿日期:  2014-02-24
  • 修回日期:  2014-09-10

6-甲氧基靛红的合成工艺改进

doi: 10.3969/j.issn.1006-0111.2015.02.009
  • 1. 沈阳药科大学制药工程学院, 辽宁 沈阳 110016;第二军医大学药学院药物化学教研室, 上海 200433
  • 2. 第二军医大学药学院药物化学教研室, 上海 200433
  • 3. 沈阳药科大学制药工程学院, 辽宁 沈阳 110016
    • 基金项目:  国家自然科学基金项目(81172928,21102174)
  • 收稿日期: 2014-02-24
  • 修回日期: 2014-09-10

摘要: 目的 探索6-甲氧基靛红的合成工艺改进方法。 方法 以3-甲氧基苯胺为起始原料,经Sandmeyer方法首先生成中间体1-肟基-N-(3-甲氧基苯基)乙酰胺,在甲磺酸催化下关环得到6-甲氧基靛红。 结果 在关环反应中,催化剂采用甲磺酸,替代文献中常用的浓硫酸,温度80℃,反应30 min,收率达81.24%。 结论 提出了一条操作简单、条件温和、收率高的6-甲氧基靛红的合成工艺,适合大量制备。

English Abstract

王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
引用本文: 王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
shu
WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
Citation: WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009
shu

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