磷酰化苯并咪唑[2,1-a ]并异喹啉衍生物的合成  

Synthesis of Phosphorylated Benzimidazo[2,1-a]Isoquinolin-6(5H)-one Derivatives

作　　者：唐裕才 黎敏 杨梦娜 黄鸿鑫 TANG Yu-cai;LI Min;YANG Meng-na;HUANG Hong-xin(Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology,Hunan Provincial Key Laboratory of Water Treatment Functional Materials,College of Chemistry and Materials Engineering,Hunan University of Arts and Science,Changde 415000,China)

机构地区：[1]湖南文理学院化学与材料工程学院水处理功能材料湖南省重点实验室电镀废水回用技术湖南省工程技术研究中心,湖南常德415000

出　　处：《化学试剂》2023年第1期169-176,共8页Chemical Reagents

基　　金：湖南省自然科学基金项目(2020JJ5390);湖南省科技创新计划资助项目(2021RC1013);湖南文理学院科学研究重点项目。

摘　　要：苯并咪唑[2,1-a]并异喹啉衍生物是一类重要的生物医药和导电高分子材料。开发其绿色的合成新方法具有重要的意义。在硝酸银为催化剂,空气为氧化剂的条件下实现了磷自由基的温和引发并应用于构建苯并咪唑[2,1-a]并异喹啉衍生物。在最佳反应条件下,以40%~65%产率合成了17种不同磷酰化苯并咪唑[2,1-a]并异喹啉化合物,采用1HNMR、^(13)CNMR对终产物进行了结构鉴定。机理验证实验表明,该反应经历了磷自由基生成、对碳碳双键加成/环化、氧化脱氢历程。该方法具有绿色环保、条件温和等优势。Benzimidazo[2,1-a]isoquinolin-6(5H)-one derivative is an important class of pharmaceutically active compounds and functional materials.It is of great scientific significance to develop a new efficient and green method for the synthesis of benzimidazo[2,1-a]isoquinolin-6(5H)-ones.In this paper,a silver catalyzed radical coupling reaction has been developed for the synthesis of benzimidazo[2,1-a]isoquinolin-6(5H)-ones under air as an oxidant.Under the optimized reaction conditions,seventeen phosphorylated benzimidazo[2,1-a]isoquinolin-6(5H)-ones were obtained with a yield of 40%~65%.Their structures were determined by 1HNMR and ^(13)CNMR.Control experiments showed that the present reaction underwent generating phosphorus radical,radical addition/cyclization and deprotonate process.This protocol has the advantages of mild condition,green and simple operations.

关 键 词：银催化 空气氧化 苯并咪唑[2 1-a]并异喹啉 磷酰化 绿色合成 

分 类 号：O626[理学—有机化学]