Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins

Molecules

Tingting Yan¹  Xiaoyan Wang²  Hongbao Sun¹  Jie Liu¹ 

[1] State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China; E-Mails:;Analytical & Testing Center, Sichuan University, Chengdu 610064, China; E-Mail:

关键词: 3-substituted-3-hydroxy-2-oxindoles;    arginine;    aldol reaction;    isatins;    α;    β-unsaturated ketones;   

DOI  :  10.3390/molecules181214505

来源: mdpi

【 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】

CC BY   
© 2006 by the authors; licensee MDPI, Basel, Switzerland.