Citation: Dao-Cai Wang, Hang Song, Chun-Yun Xu, Hui Dong, Jie Liu. Direct construction of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] through a cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals[J]. Chinese Chemical Letters, ;2015, 26(8): 1050-1053. doi: 10.1016/j.cclet.2015.04.014 shu

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

Dao-Cai Wang ^a,b ,
Hang Song ^b ,
Chun-Yun Xu ^a ,
Hui Dong ^a,b ,
Jie Liu ^a,,

1.
a State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, and Collaborative Innovation Center for Biotherapy, Chengdu 610041, China;
2.
b Department of Pharmaceutical and Biological Engineering, College of Chemical Engineering, Sichuan University, Chengdu 610065, China

Corresponding author: Jie Liu,
Received Date: 20 January 2015
Available Online: 3 April 2015
Fund Project: Financial support for this work by the National Natural Science Foundation of China (No. 81202403) (No. 81202403)

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 startingmaterials, simple experimental operation, short reaction time, as well as high yields observed.
- 3-Aminoindolin-2-one,
- Cyclization,
- 3',4'-Dihydrospiro[pyrrol-3,2'-oxindoles],
- DBU,
- Michael addition
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