有机化学 ›› 2019, Vol. 39 ›› Issue (7): 2075-2083.DOI: 10.6023/cjoc201901052 上一篇    下一篇

研究简报

温度对氮杂环卡宾催化下α-溴代烯醛与烯胺酮的[3+3]环化反应影响

王占林, 李如一, 钱辉旻, 姚昌盛   

  1. 江苏省功能材料绿色合成重点实验室 江苏师范大学化学与材料科学学院 徐州 221116
  • 收稿日期:2019-01-30 修回日期:2019-03-13 出版日期:2019-07-25 发布日期:2019-03-21
  • 通讯作者: 姚昌盛 E-mail:csyao@jsnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21871113,21372101)资助项目.

Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone

Wang Zhanlin, Li Ruyi, Qian Huimin, Yao Changsheng   

  1. Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116
  • Received:2019-01-30 Revised:2019-03-13 Online:2019-07-25 Published:2019-03-21
  • Contact: 10.6023/cjoc201901052 E-mail:csyao@jsnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21871113, 21372101).

氮杂环卡宾(NHC)催化下α-溴代烯醛和烯胺酮的[3+3]环化反应的区域选择性受温度控制.在35℃时,该反应能够区域专一性地给出稠合吡喃酮衍生物,而不是文献报道的喹啉酮类化合物.该方法反应条件温和、底物范围广、产率高、操作简便,为吡喃酮骨架的高效构建提供了新思路.

关键词: 氮杂环卡宾(NHC), α-溴代烯醛, 烯胺酮, [3+3]环化

The regioselectivity of N-heterocyclic carbene (NHC)-catalyzed[3+3] annulation of α-bromoenal with enaminone is dependent on the temperature. The reactions performed at 35℃ could regiospecifically give the derivatives of fused pyranone instead of previously reported quinolones, which provided a new shortcut to pyranone with mild reaction condition, broad substrate scope, high yields and operational simplicity.

Key words: N-heterocyclic carbene (NHC), α-bromoenal, enaminone, [3+3]annulation