N -芳基取代苯脒化合物的合成  

Synthesis of N-Aryl Substituted Benzamidine Compounds

作　　者：张翠亚 韩小娟 高艳蓉 朱周静 仝红娟 ZHANG Cuiya;HAN Xiaojuan;GAO Yanrong;ZHU Zhoujing;TONG Hongjuan(School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xianyang 712046,China;Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis,Xianyang 712046,China)

机构地区：[1]陕西国际商贸学院医药学院,陕西咸阳712046 [2]咸阳市分子影像与药物合成重点实验室,陕西咸阳712046

出　　处：《化学与生物工程》2024年第2期44-47,共4页Chemistry & Bioengineering

基　　金：陕西省自然科学基础研究计划项目(2021JQ-883,2021JQ-885);陕西高校青年科技创新团队项目(陕教[2019]90号);咸阳市分子影像与药物合成重点实验室资助项目(2021QXNL-PT-0008);陕西国际商贸学院2022年度校级科研项目(SMXY202218);陕西省教育厅2021年度一般专项科研计划项目(21JK0515)。

摘　　要：以廉价易得的苯腈(3)与取代苯胺(2a~2h)为原料,在氢化钠的碱性作用下发生亲核加成反应合成了N-芳基取代苯脒化合物(1a~1h),并对合成条件进行了优化。结果表明,以苯腈(3)与苯胺(2a)的亲核加成反应为模型,确定最优反应条件如下:物料比n(3)∶n(2a)为1.2∶1、氢化钠用量n(NaH)∶n(2a)为1.2∶1、反应溶剂为二甲基亚砜(DMSO)、反应时间为3 h,在此条件下,产物N-苯基苯脒(1a)的收率达到77%。在碘催化作用下,N-苯基苯脒(1a)可发生分子内关环反应得到2-苯基-1 H-苯并[d]咪唑(4)。该工艺反应时间短、产物收率高、底物适用性广,是合成N-芳基取代苯脒化合物的有效方法。Using cheap and easily available benzonitrile(3)and substituted aniline(2a-2h)as materials,we synthesized N-aryl substituted benzamidine compounds(1a-1h)by nucleophilic addition reaction under the alkaline action of sodium hydride.Moreover,we optimized the synthesis conditions.The results show that when the nucleophilic addition reaction between benzonitrile(3)and aniline(2a)is adopted as a model,the optimal reaction conditions are determined as follows:the material ratio n(3)∶n(2a)of 1.2∶1,the sodium hydride dosage n(NaH)∶n(2a)of 1.2∶1,dimethyl sulfoxide(DMSO)is adopted as the reaction solvent,and the reaction time of 3 h.Under above conditions,the yield of the product N-phenylbenzidine(1a)reaches 77%.Under the catalysis of iodine,2-phenyl-1 H-benzo[d]imidazole(4)can be obtained from N-phenylbenzidine(1a)by undergo intramolecular ring-closing reaction.This process has short reaction time,high product yield,and wide substrate applicability,making it an effective method for the synthesis of N-aryl substituted benzamidine compounds.

关 键 词：脒类化合物 亲核加成反应 合成 

分 类 号：TQ463[化学工程—制药化工]