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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 (CC BY 3.0).
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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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