邻甲酰基苯甲酸甲酯还原胺化/内酰胺化一锅法合成N-取代异吲哚-1-酮  

One-Pot Synthesis of N-Substituted Isoindolin-1-ones via Reductive Amination/Lactamization of Methyl 2-Formylbenzoate

作　　者：张文生 李焱[2] 崔海燕[1] 苏小莉[1] 徐素鹏[1] Zhang Wensheng;Li Yan;Cui Haiyan;Su Xiaoli;Xu Supeng(Department of Metallurgy and Chemical Engineering,Jiyuan Vocational and Technical College,Jiyuan,Henan 459000;Institute of Synthetic Technology,Jiaozuo Normal College,Jiaozuo,Henan 454100)

机构地区：[1]济源职业技术学院冶金化工系,河南济源459000 [2]焦作师范高等专科学校合成技术研究所,河南焦作454100

出　　处：《有机化学》2022年第8期2456-2461,共6页Chinese Journal of Organic Chemistry

基　　金：河南省科技攻关计划(No.212102310883);河南省教育厅自然科学重点研究(No.21B150013);济源职业技术学院自然科学重点研究(No.JZXY-2020-58)资助项目.

摘　　要：报道了一种通过邻醛基苯甲酸甲酯的胺化还原/内酰胺化一锅法合成N-取代异吲哚-1-酮的高效方法.反应包括以NaBH_(3)CN为还原剂,邻醛基苯甲酸甲酯与伯芳基胺或烷基胺的胺化还原以及N原子对羰基碳的分子内亲核进攻过程.对于4-取代芳胺、烷基胺和邻甲基苯胺,该反应可以在室温下的二氯乙烷中顺利完成转化.而其他的2-取代芳胺,则需K_(2)CO_(3)(2 equiv.)促进下在乙腈中回流8 h完成.该反应的底物适用范围很广,最高收率可达99%.An efficient,one-pot synthesis of N-substituted isoindolin-1-ones by an aminative reduction/lactamisation sequence of methyl 2-formylbenzoate is introduced.The reaction process includes aminative reduction of o-phthalaldehydic acid methylesters with primary aryl or alkyl amines using NaBH_(3)CN and the following intramolecular nucleophilic N-attack on carbonyl carbon atom.For 4-substituted aromatic amines,alkyl amines and o-methylaniline,the transformation can be successfully completed in 1,2-dichloroethane at room temperature.For other 2-substituted aromatic amines,reflux in acetonitrile for 8 h in the presence of K_(2)CO_(3)(2 equiv.)is needed.The reaction scopes were quite broad and up to 96%yield of diverse products was achieved.

关 键 词：N-取代异吲哚-1-酮 胺化还原 内酰胺化 一锅法合成 

分 类 号：O626[理学—有机化学]