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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

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Author(s): Tingting Yan | Xiaoyan Wang | Hongbao Sun | Jie Liu | Yongmei Xie

Journal: Molecules
ISSN 1420-3049

Volume: 18;
Issue: 12;
Start page: 14505;
Date: 2013;
Original page

Keywords: 3-substituted-3-hydroxy-2-oxindoles | arginine | aldol reaction | isatins | α | β-unsaturated ketones

ABSTRACT
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.
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