37118-75-5

Upstream product

• 959-66-0 3-oxo-3-phenylpropionanilide 
• 1373758-54-3 3-(4-methylphenyl)-5H-1,4,2-dioxazol-5-one 
• 412339-09-4 2-(1-phenylprop-1-en-1-yl)aniline 
• 549500-24-5 N-(2-benzoylphenyl)propionamide 
• 100-52-7 benzaldehyde 
• 60751-75-9 N-(2-iodophenyl)propionamide 
• 673-32-5 1-Phenylprop-1-yne 
• 201230-82-2 carbon monoxide 
• 62-53-3 aniline 
• 124-38-9 carbon dioxide 
• 615-43-0 2-iodophenylamine 
• 14195-24-5 4-methyl-N'-(1-phenylpropan-2-ylidene)benzenesulfonohydrazide 
• 17336-66-2 propiophenone N-tosylhydrazone 
• 34848-51-6 N-(2-(hydroxy(phenyl)methyl)phenyl)acrylamide 

Downstream Products

• 37118-76-6 2-chloro-3-methyl-4-phenylquinoline 

Relevant academic research and scientific papers

Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents

A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.

Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones

Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple, bench-top aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation. Significantly, the strategy was extended to the domino one-pot synthesis of drugs and bioactive compounds.

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.

Method for preparing 4-aryl-2-quinolinone through carbon dioxide

The invention discloses a method for preparing 4-aryl-2-quinolinone through carbon dioxide, and belongs to the technical field of carbon dioxide comprehensive utilization. The method comprises the following concrete process steps: in a dehydrated and deox

Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2towards 4-Aryl-2-Quinolinones

A palladium-catalyzed three-component reaction between N-tosylhydrazones, 2-iodoanilines and atmospheric pressure CO2was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4-aryl-2-quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C?C, one C=C and one C?N (amide), representing an efficient methodology for incorporation of CO2into heterocycles.

Intramolecular cyclization of diarylmethanols and α,β-unsaturated amides promoted by KO: T -Bu/DMF: A metal-free approach towards 3,4-disubstituted quinolinones

A facile synthesis of quinolinones through intramolecular addition of diarylmethanols to α,β-unsaturated amides promoted by KOt-Bu/DMF is reported. A series of 3,4-disubstituted quinolinones were obtained in moderate to good yields. A reaction pathway via the ketyl radical is proposed.

Synthesis of 3,4-disubstituted 2(1H)-quinolinones via intramolecular Friedel-Crafts reaction of N-arylamides of Baylis-Hillman adducts

3,4-Disubstituted 2(1H)-quinolinones were synthesized starting from the Baylis-Hillman adducts via the following sequential processes: (i) hydrolysis of the Baylis-Hillman adduct to acid, (ii) EDC coupling with anilines, (iii) H2SO4-

Facile synthesis of 4-phenylquinolin-2(1H)-one derivatives from N-acyl-o-aminobenzophenones

An efficient synthesis of 4-phenylquinolin-2(1H)-one derivatives has been achieved in a one-pot reaction from N-acyl-o-aminobenzophenones 1a-c (a: acyl=acetyl; b: acyl=propanoyl; c: acyl=heptanoyl) using NaH as a base. Treatment of 1 with NaH provided the quinolones 2a-c with 62-83% yields, whereas the reaction in the presence of alkyl iodide (alkyl=methyl, ethyl, n-octyl) gave the corresponding N-alkylated quinolones 3a-g in 75-95% yields. The alkylation reaction of 4-phenylquinolin-2(1H)-one 2a with alkyl halide gave a mixture of N-alkylated and O-alkylated products. Comparison of IR and NMR data of the N-alkylated and O-alkylated compounds with those of 2a-c indicated that 2a-c exist as the lactam form.

Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines

The palladium-catalyzed annulation of internal alkynes by N-substituted o-iodoanilines under 1 atm of carbon monoxide results in the formation of 3,4-disubstituted 2-quinolones. The nature of the substituent on the nitrogen is crucial to obtaining high yields of 2-quinolones. The best results are obtained using alkoxycarbonyl, p-tolylsulfonyl, and trifluoroacetyl substituents. The nitrogen substituent is lost during the course of the reaction resulting in the formation of N-unsubstituted 2-quinolones. A variety of internal alkynes, bearing alkyl, aryl, heteroaryl, hydroxyl, and alkoxyl substituents, are effective in this process. Electron-rich and electron-poor N-substituted o-iodoanilines, as well as heterocyclic analogues, can be employed as annulating agents.

The formation of quinolin-2(1H)-ones via electrocyclic reaction of o-isocyanatostyrenes generated in situ from o-isocyanostyrenes

A convenient one-pot preparation of 4-substituted or 3,4-disubstituted quinolin-2(1H)-ones from 2-isocyanostyrene derivatives, which involves mCPBA oxidation to the corresponding isocyanate intermediates followed by electrocyclization, is described.