布朗斯特酸催化Meyer-Schuster重排环化反应合成茚酮衍生物  

Synthesis of indenone derivatives by Br nsted acid-catalyzed Meyer-Schuster rearrangement cyclization reaction

作　　者：赵盟婷 同晓娟 张森 祝海涛 周妮妮 ZHAO Meng-ting;TONG Xiao-juan;ZHANG Sen;ZHU Hai-tao;ZHOU Ni-ni(Shannxi Key Laboratory of Phytochemistry,College of Chemistry and Chemical Engineering,Baoji University of Arts and Sciences,Baoji 721013,Shaanxi,China)

机构地区：[1]宝鸡文理学院化学化工学院,陕西省植物化学重点实验室,陕西宝鸡721013

出　　处：《宝鸡文理学院学报(自然科学版)》2024年第4期46-52,I0005-I0066,共69页Journal of Baoji University of Arts and Sciences(Natural Science Edition)

基　　金：宝鸡文理学院2022年大学生创新创业训练计划项目(S202210721038)。

摘　　要：目的发展一种原子经济的茚酮衍生物的合成方法。方法以二氯甲烷为溶剂,在布朗斯特酸的催化作用下,邻炔丙醇苯甲醛底物发生Meyer-Schuster重排环化反应,合成了一系列3-羟基茚酮衍生物。结果在最佳反应条件下,各种邻炔丙醇苯甲醛能以良好到优异的收率分别得到相应的3-羟基茚酮衍生物。该反应具有条件温和、操作简单、100%原子经济性以及克级规模合成等特点。3-羟基茚酮产物还可以通过氧化、还原以及酯化反应进行结构多样化修饰。结论开发了p-TsOH·H_(2)O催化邻炔丙醇苯甲醛的Meyer-Schuster重排环化反应,同时有效地合成了3-羟基茚酮衍生物。Purposes—To develop an atom-economic method for the synthesis of 3-hydroxyindanone derivatives.Methods—Meyer-Schuster rearrangement cyclization reaction for the synthesis of 3-hydroxyindenones from o-propargyl alcohol benzaldehydes with dichloromethane as solvent was present in the presence of Br nsted acid.Results—Under optimal reaction conditions,various o-propargyl alcohol benzaldehydes can be converted to the corresponding 3-hydroxyindanone compounds in moderate to good yields.The reaction features mild conditions,simple operation,100%atomic economy,and gram-scale synthesis.The 3-hydroxyindone products can also be modified by oxidation,reduction and esterification.Conclusions—Meyer-Schuster rearrangement cyclization reaction of o-propargyl alcohol benzaldehydes catalyzed by p-TsOH·H_(2) has been developed to effectively afford 3-hydroxyindenones.

关 键 词：Meyer-Schuster重排反应 邻炔丙醇苯甲醛 茚酮 环化反应 布朗斯特酸 

分 类 号：O621.3[理学—有机化学]