Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives.

The catalytic system generated from the cationic Ru-H complex [(CH)(PCy)(CO)RuH]BF () with 2,3,4,5-tetrachloro-1,2-benzoquinone () was found to be highly effective for promoting the deaminative coupling reaction of 2-aminoaryl aldehydes with branched amines to form 2-substituted quinoline products. The analogous deaminative coupling reaction of 2-aminoaryl ketones with branched amines led to the regioselective formation of 2,4-disubstituted quinoline products. A number of biologically active quinoline derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using the catalytic method.

Correction: Concise synthesis of 2,3-disubstituted quinoline derivatives ruthenium-catalyzed three-component deaminative coupling reaction of anilines, aldehydes and amines.

Correction for 'Concise synthesis of 2,3-disubstituted quinoline derivatives ruthenium-catalyzed three-component deaminative coupling reaction of anilines, aldehydes and amines' by Aldiyar Shakenov , , 2023, https://doi.org/10.1039/d3ob00348e.

Concise synthesis of 2,3-disubstituted quinoline derivatives ruthenium-catalyzed three-component deaminative coupling reaction of anilines, aldehydes and amines.

The Ru-H complex (PCy)(CO)RuHCl (1) was found to be a highly effective catalyst for the three-component deaminative coupling reaction of anilines with aldehydes and allylamines to form 2,3-disubstituted quinoline products. The analogous coupling reaction of anilines with aldehydes and cyclic enamines led to the selective formation of the tricyclic quinoline derivatives. The reaction profile study showed that the imine is initially formed from the dehydrative coupling of aniline and aldehyde, and it undergoes the deaminative coupling and annulation reaction with amine substrate to form the quinoline product.