Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1549-1562.DOI: 10.6023/cjoc202004039 Previous Articles     Next Articles


赵森a,b,c, 李淳朴b,c, 许斌a, 柳红b,c   

  1. a 上海大学理学院化学系 上海 200444;
    b 中国科学院上海药物研究所 新药研究国家重点实验室 上海 201203;
    c 中国科学院上海药物研究所 受体结构与功能重点实验室 上海 201203
  • 收稿日期:2020-04-25 修回日期:2020-04-30 发布日期:2020-05-08
  • 通讯作者: 许斌, 柳红;
  • 基金资助:

Cp*Rh(III)-Catalyzed C—H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]-indol-1(2H)-one Derivatives

Zhao Sena,b,c, Li Chunpub,c, Xu Bina, Liu Hongb,c   

  1. a Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444;
    b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
    c Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
  • Received:2020-04-25 Revised:2020-04-30 Published:2020-05-08
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 81620108027, 21632008, 91229204, 81220108025) and the Strategic Priority Research Program of the Chinese Academy of Sciences (Nos. XDA12020375, XDA12050411).

A mild and facile two-step strategy has been developed for the synthesis of fluorinated 3,4-dihydropyrimido-[1,6-a]-indol-1(2H)-ones through Cp*Rh(III)-catalyzed C-H 3,3-difluoroallylation and N-iodosuccinimide (NIS)-mediated cyclization. This strategy featured broad synthetic generality, unique versatility and high efficiency, which provided a potential tool for the construction of fluorine-containing heterocycles for drug discovery.

Key words: C-H activation, fluorine chemistry, rhodium catalysis