4-Phenyl-2-(1-piperazinyl)quinolines with potent antidepressant activity.

Ligand‐Enabled Triple CH Activation Reactions: One‐Pot Synthesis of Diverse 4‐Aryl‐2‐quinolinones from Propionamides

“…The use of para ‐methoxyaniline8 also allowed us to establish a new route for the deprotection of N‐substituted lactams 9. Thus, 4‐phenyl‐2‐quinolinone 3 e 1 (prepared using our newly developed one‐pot procedure) was deprotected to yield lactam 4 , which is a known precursor for the synthesis of drug molecules such as 5 10 and 6 11 (Scheme ).…”

Direct Carboxylation of C(sp3)-H and C(sp2)-H Bonds with CO2 by Transition-Metal-Catalyzed and Base-Mediated Reactions

“…As stated before the free N-H functionality was a required feature as N-CH 3 substituted indoles were inert towards carboxylation under reported conditions. The possibility for having a resonance structure with the negative charge delocalized at C3 position explains formation of the observed indole-3-carboxylic acid derivatives (146). Later, Kobayashi published the extension of the carboxylation reaction to pyrrole derivatives [141].…”

“…The 2-quinolinone motif is widely exploited in synthetic medicinal chemistry and photoelectric materials [146][147][148] and was previously accessed by the groups of Alper [149], Zhu [150] and Chuang [151] via lactamization of alkenyl and aryl C-H bonds with CO. Yu implemented, thus, a lactonization reaction using CO2 founding that 2-alkenylanilines with R 2 = CH3 (Scheme 68a) are more reactive than substrates with R 2 = H, Et. In contrast, both electron-donating and electron withdrawing substituents on the aniline nucleus do not affect significantly the substrate reactivity.…”

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

“…Thus, treatment of propionamide 156 with iodobenzene under palladium-catalyzed conditions formed intermediate 157 through sp 3 C-H arylation, dehydrogenation, and Heck reaction, followed by C-H amidation to afford quinolinone 158 in 42% yield. Removal of the 4-methoxybenzene group of 158 by treatment with BBr 3 and PIFA (bis(trifluoroacetoxy)iodo)benzene) delivered 4-phenylquinolinone 159, and the formal synthesis of the two bioactive quinoline derivatives, LTB4 antagonist [70] and MCH-1R receptor modulator [57], have been achieved from 159.…”