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Molecules 2013, 18(12), 14505-14518; doi:10.3390/molecules181214505
Article

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

1,†
,
2,†
,
1
,
1,*  and 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 These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 14 October 2013 / Revised: 15 November 2013 / Accepted: 19 November 2013 / Published: 25 November 2013
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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.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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