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

A novel tandem oxidative Ritter reaction/hydration/aldol condensation of α-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 bon...

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Published inJournal of organic chemistry Vol. 88; no. 6; pp. 3954 - 3964
Main Authors Chen, Meng-En, Gan, Zhang-Yan, Hu, Yue-Hong, Zhang, Fu-Min
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 17.03.2023
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Summary:A novel tandem oxidative Ritter reaction/hydration/aldol condensation of α-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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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02935