有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2175-2182.DOI: 10.6023/cjoc201904082 上一篇    下一篇

所属专题: 陈茹玉先生诞辰100周年

研究论文

1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化联烯的[4+2]串联反应:合成苯并噻吩并吡喃衍生物

贾继茹, 于爱敏, 刘旭光, 孟祥太   

  1. 天津市有机太阳能电池与光化学转换重点实验室 天津理工大学化学化工学院 天津 300384
  • 收稿日期:2019-04-30 修回日期:2019-06-25 发布日期:2019-07-09
  • 通讯作者: 孟祥太 E-mail:xtmeng@tjut.edu.cn
  • 基金资助:

    国家自然科学基金(No.21403154)、天津市自然科学基金(No.17JCZDJC37700)、天津市教育委(No.20180KJ137)资助项目.

1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives

Jia Jiru, Yu Aimin, Liu Xuguang, Meng Xiangtai   

  1. Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384 China
  • Received:2019-04-30 Revised:2019-06-25 Published:2019-07-09
  • Contact: 10.6023/cjoc201904082 E-mail:xtmeng@tjut.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21403154), the Natural Science Foundation of Tianjin City (No. 17JCZDJC37700) and the Tianjin Municipal Education Commission (No. 20180KJ137).

发展了1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化硫代橙酮类似物与联烯酸酯之间的串联环化反应,以甲醇为溶剂,以较好的选择性和收率获得两类苯并噻吩并吡喃衍生物.同时,该反应条件温和、底物适应性广,吸电子基或供电子基取代的硫代橙酮类似物都能以较好的选择性和收率生成目标产物.该反应为苯并噻吩并吡喃衍生物的合成提供了一种便利的方法.

关键词: 串联反应, 联烯酸酯, 苯并噻吩衍生物

A 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed[4+2] annulation reaction between 2-alkylidenebenzothio phene-3(2H)-ones and allenoate has been developed. The substrate scope includes both electron-withdrawing and electron-donating groups on the benzothiophene moiety. This method can be carried out under mild conditions and gives a wide range of highly functionalized benzothiophene-fused γ-pyran derivatives in good yields with moderate selectivity.

Key words: domino reaction, allenoate, benzothiophene derivatives