Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4789-4797.DOI: 10.6023/cjoc202107033 Previous Articles     Next Articles

ARTICLES

溶剂介导吡咯并[1,2-a]喹喔啉选择性C—H键碘代

刘亚丽, 杨振, 李阳, 刘岩*(), 刘平*()   

  1. 石河子大学化学化工学院 化工绿色过程兵团重点实验室 新疆石河子 832003
  • 收稿日期:2021-07-15 修回日期:2021-08-20 发布日期:2021-09-02
  • 通讯作者: 刘岩, 刘平
  • 基金资助:
    国家自然科学基金(21563025); 国家自然科学基金(22162022)

Solvent Mediated Selective C—H Bond Iodination of Pyrrolo[1,2-a]quinoxaline

Yali Liu, Zhen Yang, Yang Li, Yan Liu(), Ping Liu()   

  1. Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003
  • Received:2021-07-15 Revised:2021-08-20 Published:2021-09-02
  • Contact: Yan Liu, Ping Liu
  • Supported by:
    National Natural Science Foundation of China(21563025); National Natural Science Foundation of China(22162022)

A solvent mediated regioselective C—H iodination of pyrrolo[1,2-a]quinoxaline with N-iodo-succininide (NIS) has been developed. 1-Iodopyrrolo[1,2-a]quinoxalines and 3-iodopyrrolo[1,2-a]quinoxalines could be selectively synthesized by using CHCl3 and N,N-dimethylformamide (DMF) as solvents, respectively. Furthermore, 1,3-dibromopyrroloquinoxalines were obtained as the main products by the bromination of pyrrolo[1,2-a]quinoxaline with N-bromo-succinimide (NBS). The method features simple and mild reaction conditions, good regioselectivity, broad substrate scope, and gram-scale synthesis. In addition, the further transformation of halogenated pyrrolo[1,2-a]quinoxaline products has also been investigated through palladium and iodine catalyzed C—X (X=C, S) bond formation reactions.

Key words: solvent-mediated, regioselectivity, pyrrolo[1,2-a]quinoxaline, C—H bond iodination