Tandem Oxidative Ritter Reaction/Hydration/Aldol Condensation of α-Arylketones with Propiolonitriles for the Construction of 3-Acyl-3-pyrrolin-2-ones

摘要

A novel tandem oxidative Ritter reaction/hydration/aldol condensation of alpha-arylketones with substituted propiolonitriles has been developed. This protocol conveniently affords a wide range of functionalized 3-acyl-3-pyrrolin-2-ones through the efficient construction of four chemical bonds, a C-N bond, a C=C bond, and two C=O bonds, and the formation of one ring bearing an aza-quaternary center, which is ascribed to the strategical introduction of functionalized nitriles to this transformation. A reaction mechanism was proposed based on some control experiments.

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