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2022 , Vol. 42 >Issue 11: 3684 - 3692

DOI: https://doi.org/10.6023/cjoc202205030

研究论文

无金属催化的双C—H功能化N-氰基苯并咪唑合成苯并咪唑并[1,2-c]喹唑啉衍生物

  • 田晓京 ,
  • 范禛禛 ,
  • 姜思 ,
  • 李志伟 ,
  • 李江胜 ,
  • 张跃飞 ,
  • 卢翠红 ,
  • 刘卫东
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  • a长沙理工大学化学化工学院 细胞化学湖南省重点实验室 长沙 410114
    b湖南化工研究院 国家农药创制工程技术研究中心 长沙 410007

收稿日期: 2022-05-18

  修回日期: 2022-07-08

  网络出版日期: 2022-08-10

基金资助

农用化学品湖南省重点实验室开放课题(HKLA-OF2020001); 长沙市自然科学基金(kq2202185); 长沙市自然科学基金(2202184); 国家级大学生创新创业训练计划(202010536017)

收起

Metal-Free Synthesis of Benzimidazo[1,2-c]quinazolines from N-Cyanobenzimidazoles via Double C—H Functionalizations

  • Xiaojing Tian ,
  • Zhenzhen Fan ,
  • Si Jiang ,
  • Zhiwei Li ,
  • Jiangsheng Li ,
  • Yuefei Zhang ,
  • Cuihong Lu ,
  • Weidong Liu
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  • aHunan Provincial Key Laboratory of CytoChemistry, School of Chemistry and Chemical Engineering, Changsha University of Science & Technology, Changsha 410114
    bNational Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007
*E-mail: ;

Received date: 2022-05-18

  Revised date: 2022-07-08

  Online published: 2022-08-10

Supported by

Hunan Provincial Key Laboratory of Agricultural Chemicals(HKLA-OF2020001); Changsha Municipal Natural Science Foundation(kq2202185); Changsha Municipal Natural Science Foundation(2202184); National Undergraduate Training Programs for Innovation and Entrepreneurship of China(202010536017)

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摘要

在无金属、无任何添加剂的条件下, 通过过氧化物介导的双C—H功能化, 建立了一种绿色高效的合成苯并咪唑[1,2-c]喹唑啉的方法. 该方法经历了C-中心自由基和N-中心自由基之间的接力串联环化过程, 适用于多种环(硫)醚、乙二醇醚和环烷烃. 需要指出的是, 目标化合物具有良好的杀虫和杀菌活性, 特别是对粘虫具有显著的生物活性.

关键词： 双C—H功能化; 自由基串联环化; 氰胺; 苯并咪唑; 喹唑啉

本文引用格式

田晓京 , 范禛禛 , 姜思 , 李志伟 , 李江胜 , 张跃飞 , 卢翠红 , 刘卫东 . 无金属催化的双C—H功能化N-氰基苯并咪唑合成苯并咪唑并[1,2-c]喹唑啉衍生物[J]. 有机化学, 2022 , 42(11) : 3684 -3692 . DOI: 10.6023/cjoc202205030

Abstract

A green and efficient method for synthesis of privileged benzimidazo[1,2-c]quinazoline scaffolds is developed through the double C—H functionalizations mediated by peroxides under metal-free conditions without any additives. This protocol undergoes a radical cascade cyclization process involving the relay between C-centered radicals and N-centered radicals and is well applicable to a variety of cyclic (thio)ethers, glycol ethers and cyclic alkanes. Noteworthily, the title compounds display significant insecticidal and fungicidal activities, especially to armyworm.

Key words： double C—H functionalization; radical cascade cyclization; cyanamide; benzimidazole; quinazoline

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