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

Abstract

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.

Acid Catalyzed Multicomponent Reaction to Access Functionalized N‐Benzhydryl Amides: A Tandem Ritter Reaction

“…Considering the importance of the complex amide products, we assumed that readily available and less expensive nitriles would be an excellent amidation tool in tandem Ritter reaction. [32] In a classic Ritter reaction, active carbocation is produced from alcohols under acidic reaction conditions followed by reaction with nitriles to generate nitrilium ions, captured by water to finally produce amides (Figure 1). Literature reports revealed application of Ritter reaction for the synthesis of 1-amidoalkyl-2-naphthols from aryl aldehyde, phenol/2-naphthol and acetonitrile/benzonitrile in presence of Trifluoromethane sulphonic acid [33] and more recently with excess (3 equiv.)…”

Enantioselective total syntheses of six natural and two proposed meroterpenoids fromPsoralea corylifolia

“…1 n To the best of our knowledge, the total syntheses of these meroterpenes bearing four contiguous stereogenic centers have not been achieved to date. 8 Inspired by the unique structural features of the abovementioned meroterpenes and our research interest in carbonyl-related synthetic chemistry, 9 we designed a carbonyl-based conversion synthetic strategy and anticipated that these target molecules could be collectively synthesized through sequential transformations directed by the carbonyl group of synthetic intermediates in each crucial step ( Scheme 1 ). Guided by this strategy, we speculated that the structural simplification of all target meroterpenes 1a–1h to the key common intermediate 2 or its diastereomer 2′ would be feasible.…”