2584-37-4

Usage

Type of compound

Quinolinone derivative

Usage

Research as a biochemical tool or in the synthesis of other compounds

Pharmacological properties

Potential antidepressant, anxiolytic agent, and neuroprotective effects; potential role in treating neurodegenerative diseases

Other properties

Antioxidant properties; interest for studying oxidative stress and related pathways in biological systems

Interest

Therapeutic and research applications in neuroscience and pharmacology.

Upstream product

• 97038-01-2 5-methyl-2-phenyl-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one 
• 5855-57-2 4-phenyl-2-quinolinone 
• 74-88-4 methyl iodide 
• 3855-45-6 triflic azide 
• 155953-37-0 1-Methyl-2-methylene-4-phenyl-1,2-dihydro-quinoline 
• 263762-78-3 2-Eth-(E)-ylidene-1-methyl-4-phenyl-1,2-dihydro-quinoline 
• 263762-77-2 2-isopropylidene-1-methyl-4-phenyl-1,2-dihydro-quinoline 
• 263762-79-4 2-[2,2-Dimethyl-prop-(E)-ylidene]-1-methyl-4-phenyl-1,2-dihydro-quinoline 
• 7664-93-9 sulfuric acid 
• 2665-92-1 N-methyl-3-oxo-N,3-diphenylpropanamide 
• 85-99-4 2-acetamidobenzophenone 
• 32262-17-2 4-chloro-1-methyl-1H-quinolin-2-one 
• 98-80-6 phenylboronic acid 
• 110229-40-8 4-(p-toluenesulfonyloxy)-1-methyl-quinolin-2(1H)-one 

Downstream Products

• 852203-12-4 3-bromo-1-methyl-4-phenylquinolin-2(1H)-one 
• 852203-14-6 6-bromo-1-methyl-4-phenylquinolin-2(1H)-one 

Relevant academic research and scientific papers

Reversibility in Lewis-acid promoted reactions of N-arylcinnamamides

The Lewis-acid promoted cyclisation reactions of N-arylcinnamamides have been investigated. With aluminium chloride a range of products were obtained, while much more selective cyclisation reactions were observed with bismuth chloride.

Palladium-catalyzed asymmetric carbamoyl-carbonylation of alkenes

An unprecedented palladium-catalyzed asymmetric carbamoyl-carbonylation of tethered alkenes with CO and alcohols has been developed. This reaction provided an efficient route to access oxindoles and γ-lactams bearing β-carbonyl substituted quaternary carb

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Palladium-Catalyzed Cross-Coupling of Alkenyl Carboxylates

Carboxylate esters have many desirable features as electrophiles for catalytic cross-coupling: they are easy to access, robust during multistep synthesis, and mass-efficient in coupling reactions. Alkenyl carboxylates, a class of readily prepared non-aromatic electrophiles, remain difficult to functionalize through cross-coupling. We demonstrate that Pd catalysis is effective for coupling electron-deficient alkenyl carboxylates with arylboronic acids in the absence of base or oxidants. Furthermore, these reactions can proceed by two distinct mechanisms for C?O bond activation. A Pd0/II catalytic cycle is viable when using a Pd0 precatalyst, with turnover-limiting C?O oxidative addition; however, an alternative pathway that involves alkene carbopalladation and β-carboxyl elimination is proposed for PdII precatalysts. This work provides a clear path toward engaging myriad oxygen-based electrophiles in Pd-catalyzed cross-coupling.

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral

The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

A novel and facile synthesis of 4-arylquinolin-2(1H)-ones under metal-free conditions

Abstract A novel and facile synthesis of 4-arylquinolin-2(1H)-ones without metal catalysis has been developed. This reaction involved cyclization/elimination steps and was performed under metal-free conditions using inexpensive reagents such as NaI, selec

Synthesis of 3,4-disubstituted quinolin-2-(1H)-ones via palladium-catalyzed decarboxylative arylation reactions

The Pd-catalyzed decarboxylative cross-coupling reaction of 4-substituted quinolin-2(1H)-one-3-carboxylic acids with (hetero)aryl halides is described. With palladium(II) bromide and triphenylarsine ligand as the catalyst system, a variety of 4-substituted 3-(hetero)aryl quinolin-2(1 H)-ones and related heterocycles, such as 4-substituted 3-arylcoumarins can be prepared in good to excellent yields. Copyright

Synthesis of 2(1 H)-quinolinones via Pd-catalyzed oxidative cyclocarbonylation of 2-vinylanilines

Palladium-catalyzed oxidative cyclocarbonylation of N-monosubstituted-2- vinylanilines constitutes a simple, direct, and selective method for the synthesis of 2(1H)-quinolinones. The reaction conditions are attractive in terms of environmental considerations and operational simplicity. 2(1H)-Quinolinones with a variety of functional groups were prepared in up to 97% yield.

Alkyne hydroarylation with Au N-heterocyclic carbene catalysts

Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.

A versatile palladium catalyst system for Suzuki-Miyaura coupling of alkenyl tosylates and mesylates

A general and effective palladium system for Suzuki-Miyaura coupling of alkenyl electrophiles under mild reaction conditions is reported. With the Pd(OAc)2/CM-phos system, a variety of alkenyl tosylates are coupled well with ArB(OH)2. Moreover, the first successful examples of using alkenyl mesylates in alkenylation are also described.