Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 181-189.DOI: 10.6023/cjoc202107043 Previous Articles     Next Articles



钱宇亮, 许岚, 童义涵, 刘天怿, 夏盈盈, 胡顶茂, 荣良策*()   

  1. 江苏师范大学化学与材料科学学院 江苏徐州 221116
  • 收稿日期:2021-07-19 修回日期:2021-09-05 发布日期:2021-09-14
  • 通讯作者: 荣良策
  • 基金资助:
    江苏省高校自然科学研究项目(18KJA150004); 大学生创新创业训练计划和江苏省高校品牌专业建设工程资助项目

Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone)

Yuliang Qian, Lan Xu, Yihan Tong, Tianyi Liu, Yingying Xia, Dingmao Hu, Liangce Rong()   

  1. School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
  • Received:2021-07-19 Revised:2021-09-05 Published:2021-09-14
  • Contact: Liangce Rong
  • Supported by:
    Natural Science Foundation of the Jiangsu Higher Education Institutions(18KJA150004); Undergraduate Innovation and Entrepreneurship Training Program, and the Brand Major of Universities in Jiangsu Province

The efficient synthesis of 2-substituted cyclopenta[c]chromene derivatives was realized by α-C insertion of acetonitrile (acetone) with oxygen-linked 1,7-enynes catalyzed by cuprous bromide. The advantages of this reaction were wide range of substrates, high compatiblity of functional groups and good yield. The results showed that this was a radical reaction process, and it was also an effective way to construct oxygen-containing heterocycles. The X-ray diffraction analysis of 1-(4-fluorophenyl)-3a,8-dimethyl-2,3,3a,4-tetrahydrocyclopenta[c]chromene-2-carbonitrile (3am) further confirmed the structure of the product.

Key words: radical reaction, oxygen-linked 1,7-enyne, chromene, CuBr