Ruthenium-catalyzed dehydrogenative cyclization to synthesize polysubstituted 4-quinolones under solvent-free conditions?

Chemical Communications Pub Date: 2023-07-03 DOI: 10.1039/D3CC02426A

Abstract

Herein, we describe acridine-based SNS-Ru pincer-catalysed unprecedented dehydrogenative annulation of alcohols with 2′-aminoacetophenone to synthesize 2,3-disubstituted-4-quinolones. The developed protocol was utilized with a wide range of alcohols with various aminoacetophenones. To expand the synthetic utility, 4-quinolones with antibiotic properties were synthesized and various important post-synthetic modifications of the synthesized scaffolds were performed. Various control experiments were performed to understand the mechanism, which showed that C-alkylation has the edge over N-alkylation and referred to the possibility of in situ alkenylation to branched ketones.

Graphical abstract: Ruthenium-catalyzed dehydrogenative cyclization to synthesize polysubstituted 4-quinolones under solvent-free conditions
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