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

by Tingting Yan 1,†, Xiaoyan Wang 2,†, Hongbao Sun 1, Jie Liu 1,* and Yongmei Xie 1,*
1
State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China
2
Analytical & Testing Center, Sichuan University, Chengdu 610064, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2013, 18(12), 14505-14518; https://doi.org/10.3390/molecules181214505
Received: 14 October 2013 / Revised: 15 November 2013 / Accepted: 19 November 2013 / Published: 25 November 2013
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. View Full-Text
Keywords: 3-substituted-3-hydroxy-2-oxindoles; arginine; aldol reaction; isatins; α,β-unsaturated ketones 3-substituted-3-hydroxy-2-oxindoles; arginine; aldol reaction; isatins; α,β-unsaturated ketones
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MDPI and ACS Style

Yan, T.; Wang, X.; Sun, H.; Liu, J.; Xie, Y. Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins. Molecules 2013, 18, 14505-14518.

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