Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 669-676.DOI: 10.6023/cjoc202008023 Previous Articles     Next Articles


银催化的3-三氟乙酰基吲哚与异氰酸酯反应: (Z)-β-三氟甲基取代的脱氢色氨酸衍生物的高效合成

张明亮1, 赵聘1, 袁浩1, 张安安1, 张文宇1, 郑琳琳1, 吴冬青1,*(), 刘澜涛1,*()   

  1. 1 商丘师范学院化学化工学院 药物绿色合成河南省工程实验室 河南商丘 476000
  • 收稿日期:2020-08-13 修回日期:2020-09-06 发布日期:2020-09-22
  • 通讯作者: 吴冬青, 刘澜涛
  • 作者简介:
    * Corresponding authors. E-mail: ;
  • 基金资助:
    国家自然科学基金(21572126); 国家自然科学基金(21901152); 国家自然科学基金(U1904195); 河南省科技攻关(202102310003); 河南省科技攻关(192102210161); 河南省科技创新杰出人才(2018JQ0011)

Ag-Catalyzed Reactions of 3-Trifluoroacetyl Indoles and Isocyano- acetates: An Efficient Process to (Z)-β-Trifluoromethylated Dehydrotryptophan Derivatives

Mingliang Zhang1, Pin Zhao1, Hao Yuan1, An'an Zhang1, Wenyu Zhang1, Linlin Zheng1, Dongqing Wu1,*(), Lantao Liu1,*()   

  1. 1 School of Chemistry and Chemical Engineering, Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, Shangqiu Normal University, Shangqiu, Henan 476000
  • Received:2020-08-13 Revised:2020-09-06 Published:2020-09-22
  • Contact: Dongqing Wu, Lantao Liu
  • Supported by:
    the National Natural Science Foundation of China(21572126); the National Natural Science Foundation of China(21901152); the National Natural Science Foundation of China(U1904195); the Key Scientific and Technological Project of Henan Province(202102310003); the Key Scientific and Technological Project of Henan Province(192102210161); the Science and Technology Innovation Talents of Henan Province(2018JQ0011)

Catalytic cyclization-rearrangement reaction of 3-trifluoroacetyl indole and isocyanoacetate was achieved with AgOAc as catalyst in mild conditions. A serious of β-trifluoromethylated dehydrotryptophan derivatives were obtained with single Z-isomer in excellent yields (up to >99% yields). The large scale experiment proceeded smothly genereting desired products in up to 98% isolated yield, which demostrated the practicality of the method. The plausible mechanism was aslo proposed. This transformation has features of high atom economy, mild reaction condition and easy operation.

Key words: 3-trifluoroacetyl indole, isocyanoacetate, dehydrotryptophan