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Mild Direct Single-Step Conversion of Propargyl Amines to Highly Substituted 3-Pyrrolin-2-ones
Mina C Nakhla1, John L Wood2, Michael G Organ1
1Department of Chemistry and Biomolecular Sciences, Centre for Catalysis Research and Innovation (CCRI), University of Ottawa, Ottawa, Ontario K1N 6N5, Canada.
Abstract:
Pyrrolinones are frequently found in biologically active natural products and pharmaceuticals. As such, their synthesis has been the focus of several methodological studies. Described herein is a synthetic method for the direct conversion of terminal or arylated propargyl amines to 3-pyrrolin-2-ones utilizing a malonyl chloride and an amine base at a low temperature. It is postulated that the key intermediate is an ammonium enolate generated during the initial premixing of the amine base and malonyl chloride.
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