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2021 , Vol. 41 >Issue 2: 669 - 676

DOI: https://doi.org/10.6023/cjoc202008023

研究论文

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 ,
  • 赵聘 ,
  • 袁浩 ,
  • 张安安 ,
  • 张文宇 ,
  • 郑琳琳 ,
  • 吴冬青 ,
  • 刘澜涛
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  • 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
* Corresponding authors. E-mail: ;

收稿日期: 2020-08-13

  修回日期: 2020-09-06

  网络出版日期: 2020-09-22

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)

收起

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

  • Mingliang Zhang ,
  • Pin Zhao ,
  • Hao Yuan ,
  • An'an Zhang ,
  • Wenyu Zhang ,
  • Linlin Zheng ,
  • Dongqing Wu ,
  • Lantao Liu
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  • 1 School of Chemistry and Chemical Engineering, Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, Shangqiu Normal University, Shangqiu, Henan 476000

Received date: 2020-08-13

  Revised date: 2020-09-06

  Online published: 2020-09-22

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)

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摘要

实现了银催化的3-三氟乙酰基吲哚与异氰酸酯的环化-重排反应, 以优秀的收率(up to >99%)得到了一系列单一构型的( Z)-β-三氟甲基脱氢色氨酸衍生物. 反应以克级规模进行时, 产率仍能达到98%, 这一结果证明了反应的实用性. 此外, 作者提出了可能的反应机理. 该反应具有原子经济性高、反应条件温和及操作简便等优点.

关键词： 3-三氟乙酰基吲哚; 异氰酸酯; 脱氢色氨酸

本文引用格式

张明亮 , 赵聘 , 袁浩 , 张安安 , 张文宇 , 郑琳琳 , 吴冬青 , 刘澜涛 . 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[J]. 有机化学, 2021 , 41(2) : 669 -676 . DOI: 10.6023/cjoc202008023

Abstract

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

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