Direct construction of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles]through a cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals  

作　　者：Dao-Cai Wang Hang Song Chun-Yun Xu Hui Dong Jie Liu 

机构地区：[1]State Key Laboratory of Biotherapy and ]Cancer Center, West China Hospital, Sichuan University, and Collaborative Innovation Center for Biotherapy [2]Department of Pharmaceutical and Biological Engineering, College of Chemical Engineering, Sichuan University

出　　处：《Chinese Chemical Letters》2015年第8期1050-1053,共4页中国化学快报（英文版）

基　　金：Financial support for this work by the National Natural Science Foundation of China(No.81202403);West China HospitalChengdu Science and Technology Department Translational Medicine Innovation Foundation(No.ZH13039)

摘　　要：A simple and efficient cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals was identified for the synthesis of potentially biologically active 3＇,4＇-dihydrospiro[pyrrol-3,2＇-oxindoles], using DBU as an efficient catalyst and ethylene glycol as an environmentally benign solvent. More diverse 3＇,4＇-dihydrospiro[pyrrol-3,2＇-oxindoles] analog libraries were prepared in good yields（up to 97%）. The structure of 3＇,4＇-dihydrospiro[pyrrol-3,2＇-oxindoles] was confirmed by mass spectrometry analysis, NMR analysis and single crystal X-ray diffraction. The main advantages of this method include the availability of starting materials, simple experimental operation, short reaction time,as well as high yields observed.A simple and efficient cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals was identified for the synthesis of potentially biologically active 3＇,4＇-dihydrospiro[pyrrol-3,2＇-oxindoles], using DBU as an efficient catalyst and ethylene glycol as an environmentally benign solvent. More diverse 3＇,4＇-dihydrospiro[pyrrol-3,2＇-oxindoles] analog libraries were prepared in good yields（up to 97%）. The structure of 3＇,4＇-dihydrospiro[pyrrol-3,2＇-oxindoles] was confirmed by mass spectrometry analysis, NMR analysis and single crystal X-ray diffraction. The main advantages of this method include the availability of starting materials, simple experimental operation, short reaction time,as well as high yields observed.

关 键 词：cyclization glycol cascade starting analog biologically diverse potentially pyrrolidine spiro 

分 类 号：TQ251.34[化学工程—有机化工]