基于Fries-Schmidt串联反应的对羟基苯甲酰四氢吡咯的合成及初步机制研究  

Synthesis and Preliminary Mechanism Study of(4-Hydroxyphenyl)-1-Pyrrolidinylmethanone Based on a Landem Fries-Schmidt Reaction

作　　者：王丽楠 范梅霞 戚君慧 姚雷[1] WANG Li-nan;FAN Mei-xia;QI Jun-hui;YAO Lei(School of Pharmacy,Key Laboratory of Molecular Pharmacology and Drug Evaluation(Yantai University),Ministry of Education Collaborative Innovation Center of AdvancedDrug Delivery System and Biotech Drugs in Universities of Shandong,Yantai University,Yantai 264005,China)

机构地区：[1]烟台大学分子药理和药物评价教育部重点实验室,新型制剂与生物技术药物研究山东省高校协同创新中心,山东烟台264005

出　　处：《烟台大学学报（自然科学与工程版）》2021年第1期16-21,共6页Journal of Yantai University(Natural Science and Engineering Edition)

基　　金：烟台大学博士基金资助项目(YX13B04)。

摘　　要：以四氯化钛为路易斯酸催化剂,在1,2-二氯乙烷作为溶剂回流的条件下,5-叠氮基戊酸苯酯通过串联的Fries-Schmidt反应成功地制备了对羟基苯甲酰四氢吡咯,产率为66%。研究了酸催化剂的种类及用量、溶剂、温度对串联反应的影响,通过平行试验筛选了串联反应的最优条件。通过设计对照实验初步研究了Fries-Schmidt串联反应可能的反应机制。此串联反应具有用时短、收率高和操作简单等优点。Treatment of phenyl 5-azidovalerate with TiCl 4under 1,2-dichloroethane refluxing condition,(4-Hydroxyphenyl)-1-pyrrolidinylmethanone is successfully prepared by a tandem Fries-Schmidt reaction,and the yield is 66%.The reaction parameters,including type and amount of catalyst,solvent,and temperature,are discussed and the optimal condition is also screened by parallel experiments.The possible mechanism of the tandem Fries-Schmidt reaction is proposed and preliminarily studied by a control experiment.This tandem reaction has advantages of time saving,high yield and simple operation.

关 键 词：串联反应 Schmidt反应 Fries反应 芳酰胺 对羟基苯甲酰四氢吡咯 

分 类 号：O621.3[理学—有机化学]