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  

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

作　　者：田晓京 范禛禛 姜思 李志伟[1] 李江胜[1] 张跃飞[1] 卢翠红 刘卫东[2] Tian Xiaojing;Fan Zhenzhen;Jiang Si;Li Zhiwei;Li Jiangsheng;Zhang Yuefei;Lu Cuihong;Liu Weidong(Hunan Provincial Key Laboratory of CytoChemistry,School of Chemistry and Chemical Engineering,Changsha University of Science&Technology,Changsha 410114;National Engineering Research Center for Agrochemicals,Hunan Research Institute of Chemical Industry,Changsha 410007)

机构地区：[1]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 [2]湖南化工研究院国家农药创制工程技术研究中心,长沙410007

出　　处：《有机化学》2022年第11期3684-3692,共9页Chinese Journal of Organic Chemistry

基　　金：农用化学品湖南省重点实验室开放课题(No.HKLA-OF2020001);长沙市自然科学基金(Nos.kq2202185,2202184);国家级大学生创新创业训练计划(No.202010536017)资助项目.

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.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.

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 

分 类 号：O626[理学—有机化学]