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2024 , Vol. 44 >Issue 9: 2820 - 2831

DOI: https://doi.org/10.6023/cjoc202403020

研究论文

二氟甲基取代的1,2,4-三氮唑啉化合物的合成

  • 樊莹 ,
  • 黄丹凤 ,
  • 马虎 ,
  • 白祖瑜 ,
  • 王克虎 ,
  • 王君姣 ,
  • 胡雨来
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  • 西北师范大学化学化工学院 兰州 730070

收稿日期: 2024-03-15

  修回日期: 2024-05-07

  网络出版日期: 2024-05-23

基金资助

国家自然科学基金(22061037); 国家自然科学基金(21861033); 上海恩氟佳科技有限公司资助项目

收起

Synthesis of Difluoromethyl Substituted 1,2,4-Triazoline Compounds

  • Ying Fan ,
  • Danfeng Huang ,
  • Hu Ma ,
  • Zuyu Bai ,
  • Ke-Hu Wang ,
  • Junjiao Wang ,
  • Yulai Hu
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  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
*E-mail: ;

Received date: 2024-03-15

  Revised date: 2024-05-07

  Online published: 2024-05-23

Supported by

National Natural Science Foundation of China(22061037); National Natural Science Foundation of China(21861033); Shanghai Sinofluoro Chemicals Co., Ltd.

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摘要

探索了在碱的作用下, 由二氟甲基溴代腙原位生成的二氟甲基腈亚胺与3-亚胺基氧化吲哚的1,3-偶极环加成反应. 在温和的反应条件下, 以高达97%的产率和优异的区域选择性成功地合成了37个二氟甲基取代的螺1,2,4-三氮唑啉氧化吲哚类化合物. 该方法为合成二氟甲基取代的1,2,4-三氮唑啉化合物提供了一种新方法, 进一步拓展了二氟甲基腈亚胺在1,3-偶极环加成反应中的应用范围

关键词： 1,2,4-三氮唑啉; 二氟甲基; 二氟甲基溴代腙; 1,3-偶极环加成; 合成

本文引用格式

樊莹 , 黄丹凤 , 马虎 , 白祖瑜 , 王克虎 , 王君姣 , 胡雨来 . 二氟甲基取代的1,2,4-三氮唑啉化合物的合成[J]. 有机化学, 2024 , 44(9) : 2820 -2831 . DOI: 10.6023/cjoc202403020

Abstract

A 1,3-dipolar cycloaddition of difluoromethyl nitrile imines generated in situ from difluoroacetohydrazonoyl bromides with 3-iminooxindoles in the presence of base is described. Under mild reaction conditions, thirty-seven difluoro- methyl substituted spiro 1,2,4-triazoline oxindole compounds were successfully synthesized in up to 97% yield with excellent regioselectivity. This method provides a new method for the synthesis of difluoromethyl substituted 1,2,4-triazoline compounds, and further expands the application range of difluoromethyl nitrile imines in 1,3-dipolar cycloaddition reactions

Key words： 1,2,4-triazolines; difluoromethyl; difluoroacetohydrazonoyl bromides; 1,3-dipolar cycloaddition; synthesis

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