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Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2015  >  33(2): 127-130

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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Improvement of synthesis method of 6-methoxyisatin

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

  • Received Date: 2014-02-24
  • Rev Recd Date: 2014-09-10
  • 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.
  • [1] Guo Y, Chen F. TLC-UV-spectrophotometric and TLCscanning determination of isatin in leaf of Isatis[J]. Zhongcaoyao, 1986, 17(2): 8-11.
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    [3] Galliford CV, Scheidt KA.Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents[J]. Angew Chem Int Ed Engl, 2007, 46(46): 8748-8758.
    [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.
    [12] Parsy CC,Surleraux D,Alexandre FR,et al.Macrocyclic serine protease inhibitors I[P].美国,20090047244,2009-02-19.
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Improvement of synthesis method of 6-methoxyisatin

doi: 10.3969/j.issn.1006-0111.2015.02.009
  • 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
  • Received Date: 2014-02-24
  • Rev Recd Date: 2014-09-10

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.

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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