Journal
MOLECULES
Volume 18, Issue 12, Pages 14505-14518Publisher
MDPI AG
DOI: 10.3390/molecules181214505
Keywords
3-substituted-3-hydroxy-2-oxindoles; arginine; aldol reaction; isatins; alpha,beta-unsaturated ketones
Funding
- National Natural Science Foundation of China [81202403]
- Youth Foundation of Sichuan University [2012SCU11090, 2011SCU11005]
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An efficient approach for the synthesis of 3-substituted-3-hydroxy-2-oxindoles has been achieved via an aldol reaction of alpha,beta-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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