Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

“…[55] 3-Acetylisoqulinoline was prepared from 3-hydroxyisoqulinoline by a Heck reaction. [56] 1-(2-(3'-Isoquinolinyl)-2-oxoethyl)pyridinium iodide was prepared by heating 3-acetylisoqulinoline with excess I 2 in pyridine for 2 h. [57][58][59] 3-Dimethylamino-1-(2'-naphthyl)propanone hydrochloride salt was synthesized by refluxing 2-acetylnaphthalene, paraformaldehyde and dimethylamine hydrochloride in the presence of conc. HCl in 95 % ethanol for 24 h. [59] The a,b-unsaturated ketones were prepared according to literature methods.…”

A Green, Solvent-Free One-Pot Synthesis of Disubstituted Quinolines via A3-Coupling Using 1 Mol% FeCl3

“…reacted 2-chloroquinoline 28 with 1-ethoxy-2-tributylstannylester in the presence of Pd(dba)2/PPh4 to produce 2-(1-acetyl)quinoline 29 (Scheme 13). [49] Scheme 13: Stille cross-coupling reaction for the synthesis of quinolines. quinoline were observed, (34-48%) due to the formation of side products such as the reduced imine and uncyclized propargylamine.…”

Pyrido[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-diones: Synthesis, Cyclometalation, and Protein Kinase Inhibition

“…The synthetic route is also applicable to derivative 20 in which the pyridine ring is replaced by an isoquinoline. Starting with 3-acetylisoquinoline (21), 16 hydrazone formation to 22 and subsequent Fischer indole synthesis provided the isoquinolinoindole 23 in yields of 40% over the two steps. Compound 23 was lithiated with LiHMDS and reacted with one equivalent of dibromomaleimide 11 to yield the monobromide substitution product 24 which was directly photocyclized under argon to 20 (84% yield over both steps) (Scheme 3).…”