Molecules | |
Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins | |
Xiaoyan Wang1  Tingting Yan2  Hongbao Sun2  Jie Liu2  Yongmei Xie2  | |
[1] Analytical & Testing Center, Sichuan University, Chengdu 610064, China;State Key Laboratory of Biotherapy, West China Hospital, West China Medical School,Sichuan University, Chengdu 610041, China; | |
关键词: 3-substituted-3-hydroxy-2-oxindoles; arginine; aldol reaction; isatins; α,β-unsaturated ketones; | |
DOI : 10.3390/molecules181214505 | |
来源: DOAJ |
【 摘 要 】
An efficient approach for the synthesis of 3-substituted-3-hydroxy-2-oxindoles has been achieved via an aldol reaction of α,β-unsaturated ketones and isatins using arginine as an organocatalyst. A range of 3-substituted-3-hydroxy-2-oxindoles were obtained in moderate to high (up to 99%) yields. These 3-substituted-3-hydroxy-2-oxindoles with an additional enone moiety provide an opportunity for further elaboration of the products and for potentially interesting biological activities. In addition, the formation of 3-substituted-3-hydroxy-2-oxindole 3a was confirmed by X-ray crystallography. The possible reaction mechanism reveals that the reaction proceeds via a double action process.
【 授权许可】
Unknown