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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (04): 563-567. 上一篇    下一篇

研究简报

取代吲哚-3-甲醛类化合物的合成

葛裕华*，吴亚明，薛忠俊   

  1. (Department of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096)
  • 收稿日期:2005-06-08 修回日期:2005-10-31 发布日期:2006-03-31
  • 通讯作者: 葛裕华

Synthesis of Substituted Indole-3-carboxaldehyde Derivatives

GE Yu-Hua*,WU Ya-Ming,XUE Zhong-Jun   

  • Received:2005-06-08 Revised:2005-10-31 Published:2006-03-31
  • Contact: GE Yu-Hua

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被引次数

75 | 21

取代邻硝基甲苯(1)、N,N-二甲基甲酰胺二甲基缩醛或二乙基缩醛和哌啶在溶剂N,N-二甲基甲酰胺中缩合制得取代的β-哌啶基-2-硝基甲苯(2), 2用铁粉和冰醋酸还原环合得到取代吲哚(3), 将3与三氯氧磷和N,N-二甲基甲酰胺通过Vilsmeier-Hacck反应制得了取代吲哚-3-甲醛类化合物4和5. 化合物4和5的结构经元素分析, IR和1H NMR确认.

关键词: 取代吲哚-3-甲醛, 合成, Vilsmeier-Hacck反应

Substituted 2-nitro-β-piperidinostyrenes (2), obtained from the reaction of substituted 2-nitrotoluene (1), N,N-dimethylformamide dimethyl acetal or N,N-dimethylformamide diethyl acetal and piperidine in solvent of N,N-dimethylformamide, reacted with iron and acetic acid to yield the substituted indoles 3. Substituted indole-3-carboxaldehydes 4 and 5 were synthesized from 3 by Vilsmeier-Hacck reaction with phosphorus oxychloride and N,N-dimethylformamide. The structures of 4 and 5 were analyzed and established by elemental analysis, IR and 1H NMR spectra.

Key words: synthesis, substituted indole-3-carboxaldehyde, Vilsmeier-Hacck reaction