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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (06): 890-893. 上一篇    下一篇

研究简报

Ugi/SmI2还原反应合成N-取代β,γ-不饱和酰胺的研究

于辉*，孙文亮，高瑞，章美束   

  1. 同济大学化学系 上海 200092
  • 收稿日期:2009-07-08 修回日期:2009-09-03 发布日期:2010-01-04
  • 通讯作者: 于辉 E-mail:yuhui@tongji.edu.cn
  • 基金资助:

    教育部留学回国人员基金

A Facile Route to the Synthesis of N-Substituted β,γ-Unsaturated Amides by Ugi/SmI2 Reduction

YU Hui, SUN Wen-Liang, GAO Rui, ZHANG Mei-Shu   

  1. Department of Chemistry, Tongji University, Shanghai 200092
  • Received:2009-07-08 Revised:2009-09-03 Published:2010-01-04
  • Contact: Yu Hui E-mail:yuhui@tongji.edu.cn

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将α,β-不饱和醛、苯胺、乙酸和异腈的Ugi四组分反应产物在四氢呋喃中用SmI2/HMPA处理, 可以得到碳链延长一位的β,γ-不饱和酰胺, 方法简便, 产率中等到良好. 该反应涉及一个自由基脱氨基过程.

关键词: 异腈, Ugi, 多组分反应, 二碘化钐

A novel way to the synthesis of β,γ-unsaturated amides was explored by treating the Ugi adducts of α,β-unsaturated aldehydes, isocyanides, aniline and acetic acid with SmI2/HMPA in dry tetrahydrofuran at room temperature. The yields were moderate to good. This reaction involved the radical deamination of α-substituted amides.

Key words: isocyanide, Ugi, multicompound reaction, samarium diiodide