Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1778-1785.DOI: 10.6023/cjoc202111031 Previous Articles     Next Articles



李芳绍, 肖晶*(), 吴小芳, 王晓熠, 邓金凤, 唐子龙*()   

  1. 湖南科技大学化学化工学院 理论有机化学与功能分子教育部重点实验室 湖南湘潭 411201
  • 收稿日期:2021-11-22 修回日期:2022-02-08 发布日期:2022-02-25
  • 通讯作者: 肖晶, 唐子龙
  • 基金资助:
    国家自然科学基金(21703061); 湖南省科技创新计划(2021RC5028)

Metal-Free Formation of 2-Substitued Benzoxazoles with Amides and Esters

Fangshao Li, Jing Xiao(), Xiaofang Wu, Xiaoyi Wang, Jinfeng Deng, Zilong Tang()   

  1. Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
  • Received:2021-11-22 Revised:2022-02-08 Published:2022-02-25
  • Contact: Jing Xiao, Zilong Tang
  • Supported by:
    National Natural Science Foundation of China(21703061); Science and Technology Innovation Program of Hunan Province(2021RC5028)

2-Substituted benzoxazoles are important heterocyclic motifs due to their wide application in pharmacology. A PCl3-mediated C(2)-functionalization of benzoxazole derivatives with inert amides and esters under metal-free conditions was reported. By using PCl3/I2 combination, various 2-substituted benzoxazoles could be synthesized via the arylation or alkylation of benzoxazoles with amides and esters in the presence of water. What’s more, the reactivity between amides and esters was also investigated. The primary results indicated that amides have higher reactivity than esters under this system. This method features a broad substrate scope, simple condition and low-cost. A plausible mechanism was also proposed.

Key words: 2-substituted benzoxazoles, amide, ester, metal-free, phosphorus trichloride