ArticleChemical science2023
Rh(iii)-catalyzed highly site- and regio-selective alkenyl C-H activation/annulation of 4-amino-2-quinolones with alkynes
Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
3,4-Fused 2-quinolone frameworks are important structural motifs found in natural products and biologically active compounds. Intermolecular alkenyl C-H activation/annulation of 4-amino-2-quinolone substrates with alkynes is one of the most efficient methods for accessing such structural motifs. However, this is a formidable challenge because 4-amino-2-quinolones have two cleavable C-H bonds: an alkenyl C-H bond at the C3-position and an aromatic C-H bond at the C5-position. Herein, we report the Rh(iii)-catalyzed highly site-selective alkenyl C-H functionalization of 4-amino-2-quinolones to afford 3,4-fused 2-quinolones. This method has a wide substrate scope, including unsymmetrical internal alkynes, with complete regioselectivity. Several control experiments using an isolated key intermediate analog suggested that the annulation reaction proceeds
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