19069-84-2

Upstream product

• 41296-66-6 2'-acetyl-1-phenylacetanilide 
• 2142-69-0 2-bromophenyl methyl ketone 
• 103-81-1 Benzeneacetamide 
• 551-93-9 2-aminoacetophenone 
• 124-38-9 carbon dioxide 
• 673-32-5 1-Phenylprop-1-yne 
• 201230-82-2 carbon monoxide 
• 62-53-3 aniline 
• 607-66-9 4-methyl-1,2-dihydroquinolin-2-one 
• 59-88-1 phenylhydrazine hydrochloride 
• 103-82-2 phenylacetic acid 
• 2142-70-3 2-iodoacetophenone 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 166538-06-3 N-(2-Acetyl-phenyl)-2-oxo-2-phenyl-acetamide 

Downstream Products

• 89081-24-3 Dimethyl-[2-(4-methyl-3-phenyl-quinolin-2-ylsulfanyl)-ethyl]-amine 
• 89081-06-1 2-chloro-4-methyl-3-phenylquinoline 

Relevant academic research and scientific papers

Rh-catalyzed aerobic oxidative cyclization of anilines, alkynes, and CO

Transition-metal-catalyzed oxidative C-H cyclization of anilines has been an attractive and powerful strategy for the efficient construction of N-heterocycles. However, primary and tertiary anilines are rarely employed in this strategy due to the relative instability with strong oxidants or the presence of three C-N bonds. We describe here a novel Rh-catalyzed C-H cyclization of a wide range of anilines with alkynes and CO, using an aerobic oxidative protocol. Particularly, the simple primary anilines and readily prepared tertiary anilines could be easily converted to quinolin-2(1H)-ones, which are high value-added, biologically significant N-heterocycles, via C-N bond cleavage.

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.

Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions

A facile regioselective metal-free direct α-arylation of coumarins and 2-pyridones is achieved by the reaction of coumarins and 2-pyridones with phenylhydrazine in good yields. The reaction proceeds at room temperature under mild conditions using inexpensive reagents and without the need for step intensive activating groups. The methodology is operationally simple, practically viable and also allows the coupling of similar nitrogen heterocycle aza-coumarins without prerequisite N-protection.

3-Aryl-4-methyl-2-quinolones Targeting Multiresistant Staphylococcus aureus Bacteria

The NorA efflux pump lowers intracellular fluoroquinolone concentrations by expelling antibiotics through the membrane of Staphylococcus aureus. We identified 3-aryl-4-methyl-2-quinolin-2-ones as compounds able to restore the activity of the NorA substrate, ciprofloxacin, against resistant S.aureus strains, and acting as efflux pump inhibitors (EPI). In particular, 5-hydroxy-7-methoxy-4-methyl-3-phenylquinolin-2-one (6c) presents both an EPI and an antimicrobial effect. Its efficacy and safety make it a potential candidate for further investigations.

Copper(I) iodide catalyzed synthesis of quinolinones via cascade reactions of 2-halobenzocarbonyls with 2-arylacetamides

An efficient copper-catalyzed method for the synthesis of quinolinones, pyridinones, and heteroannulated pyridinones via cascade reactions of substituted 2-iodo-, 2-bromo-, and 2-chlorobenzocarbonyls with 2-arylacetamides is reported. The protocol works well for the reaction of most of the 2-iodo-, 2-bromo- and 2-chlorobenzocarbonyls with 2-arylacetamides. Georg Thieme Verlag Stuttgart · New York.

A new synthesis of naphthyridinones and quinolinones: Palladium-catalyzed amidation of o-carbonyl-substituted aryl halides

(Equation Presented) An alternative to the Friedlander condensation for the synthesis of naphthyridinones and quinolinones has been discovered. Palladium-catalyzed amidation of halo aromatics substituted in the ortho position by a carbonyl functional group or its equivalent with primary or secondary amides leads to the formation of substituted naphthyridinones and quinolinones.

N-3-oxoalkylamides and -thioamides in synthesis of heterocyclic compounds. 4. Synthesis of hydrogenated derivatives of quinoline and isoquinoline based on N-3-oxoalkylamides

Hydrogenated derivatives of quinoline and isoquinoline were obtained by cyclization of N-3-oxoalkylamides with bases. 1998 Plenum Publishing Corporation.

Synthesis of Coumarins and Quinolones by Intramolecular Aldol Condensation Reactions of Titanium Enediolates

Low-valent titanium prepared by the reduction of TiCl3 with zinc dust oxidatively adds to α-ketoamides or α-ketoesters with the formation of the corresponding titanium enediolates.These 1,2-difunctional nucleophiles, which have hardly been used in organic

Synthesis and 5-Hydroxytryptamine Antagonist Activity of 2-thio>-3-phenylquinoline and Its Analogues

A series of 2-quinolines substituted at the 3-position with alkyl, aryl, or heteroaryl groups has been prepared in the search for novel and selective 5-HT2 antagonists.The affinity of the compounds for 5-HT1 recep