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Base-Mediated Intramolecular Cyclization of α‑Nitroethylallenic Esters as a Synthetic Route to 5‑Hydroxy-3-pyrrolin-2-ones

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journal contribution
posted on 01.04.2021, 10:25 by Narendra Kumar Vaishanv, Mohd Khalid Zaheer, Sandeep Kumar, Ruchir Kant, Kishor Mohanan
An unprecedented Cs2CO3-mediated intramolecular cyclization/rearrangement cascade that transforms α-nitroethylallenic esters to functionalized pyrrolin-2-ones has been uncovered. This reaction provides a new and practical approach for the synthesis of medicinally privileged 5-hydroxy-3-pyrrolin-2-ones under mild conditions. The broad potential of this new method was demonstrated by an efficient Au/Ag-catalyzed heteroarylation of 5-hydroxy-3-pyrrolin-2-ones employing electron-rich heteroarenes to furnish heteroaryl-lactam derivatives.

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