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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (05): 648-654. 上一篇    下一篇

综述与进展

2(5H)-呋喃酮与含氮亲核试剂反应研究进展

宋秀美1,2,3，李建晓1，汪朝阳*,1，莫阳青1   

  1. (1华南师范大学化学与环境学院 广州 510006)
    (2广东高校新材料工程技术开发中心 湛江 524048)
    (3湛江师范学院化学系 湛江 524048)
  • 收稿日期:2009-07-27 修回日期:2009-09-03 发布日期:2009-11-03
  • 通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com
  • 基金资助:

    国家级.国家自然科学基金

Progress in Reactions of 2(5H)-Furanone with Nucleophiles Containing Nitrogen

Song Xiumei1,2,3 Li Jianxiao1 Wang Zhaoyang*,1 Mo Yangqing1   

  1. (1 Department of Chemistry, South China Normal University, Guangzhou 510006)
    (1 Development Center for New Materials Engineering & Technology in Universities of Guangdong, Zhanjiang 524048)
    (3 Department of Chemistry, Zhanjiang Normal College, Zhanjiang 524048)
  • Received:2009-07-27 Revised:2009-09-03 Published:2009-11-03
  • Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

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2(5H)-呋喃酮作为一种α,β-不饱和环丁内酯, 可发生多种反应, 特别是其不饱和碳碳双键上连有卤素时, 2(5H)-呋喃酮的高反应性使其被广泛应用于有机合成. 按照反应后五元环内酯产物上取代基位置的不同, 综述了2(5H)-呋喃酮与含氮亲核试剂通过Michael加成、串联的Michael加成-消除、偶极环加成和钯催化耦合等反应合成β-取代、α,β-取代和γ-取代环状衍生物在近十几年的研究进展.

关键词: 2(5H)-呋喃酮, 含氮亲核试剂, Michael加成, 偶极环加成, 串联反应

As a kind of α,β-unsaturated butyrolactone, 2(5H)-furanone is so reactive in lots of reactions that it has been used extensively in organic synthesis, especially, when a halogen atom is attached to the C＝C unsaturated bond. According to the different reaction points, the recent advance in reactions of 2(5H)-furanone with nucleophiles containing nitrogen to give cyclic derivatives with β-substituent, α,β-disubstituents or γ-substituent via Michael addition, tandem Michael addition-elimination, dipolar cycloaddition or palladium-catalyzed cross-coupling reactions is reviewed.

Key words: 2(5H)-furanone, nucleophile containing nitrogen, Michael addition, dipolar cycloaddition, tandem reaction