Base-catalyzed reaction between isatins and N-Boc-3-pyrrolin-2-one |
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Authors: | Naresh Ramireddy John C-G Zhao |
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Institution: | Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0698, USA |
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Abstract: | The base-catalyzed reaction between isatins and N-Boc-3-pyrrolin-2-one yields Morita–Baylis–Hillman (MBH) adducts instead of the expected aldol products in good to high yields (up to 97%). Various organic and inorganic bases are efficient catalysts for this reaction. Our study excluded the Morita–Baylis–Hillman mechanism for the formation of the MBH-type products. The MBH products are most likely formed as a result of the subsequent isomerization of the original aldol products between isatins and N-Boc-3-pyrrolin-2-one. |
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Keywords: | Isatin 3-Pyrrolin-2-one Catalysis Mechanism Morita&ndash Baylis&ndash Hillman reaction |
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