30169-33-6

Usage

Biological activities

anti-inflammatory, anti-tumor, antifungal effects
Substitution of chlorine and a phenyl ring
Unique chemical and biological properties
Promising candidate for new therapeutic agents
Interesting structural features
Valuable scaffold for designing novel drugs

Upstream product

• 962-08-3 N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide 
• 13788-59-5 N-(2-benzoyl-4-chlorophenyl)acetamide 
• 127-19-5 N,N-dimethyl acetamide 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 31576-98-4 6-Chlor-2-dimethylamino-4-phenylchinolin 
• 76303-82-7 9-Chlor-2,3-dihydro-5-methyl-10b-phenyl-10bH-oxazolo<3,2-c>chinazolin 
• 141-78-6 ethyl acetate 
• 77-78-1 dimethyl sulfate 
• 20028-53-9 2-amino-5-chlorobenzaldehyde 
• 3158-98-3 1-(2-amino-5-chlorophenyl)-1-phenylethan-1-ol 
• 1685-19-4 2-amino-5-chloroacetophenone 
• 100-58-3 phenylmagnesium bromide 
• 66003-76-7 Diphenyliodonium triflate 
• 611-73-4 Benzoylformic acid 

Downstream Products

• 10352-30-4 2,6-dichloro-4-phenylquinoline 
• 36271-04-2 6-chloro-1-methyl-4-phenylquinolin-2(1H)-one 
• 1314518-65-4 C₆₈H₆₂Cl₂N₆O₂ 
• 1314518-72-3 C₆₈H₆₀B₂Cl₂F₄N₆O₂ 
• 1314518-54-1 tert-butyl (2Z)-2-[6-chloro-4-phenylquinolin-2(1H)-ylidene]-2-cyanoacetate 
• 1314518-56-3 (6-chloro-4-phenylquinolin-2-yl)acetonitrile 
• 32676-11-2 6-chloro-4-phenyl-2-(4-phenyl-piperazin-1-yl)-quinoline 
• 31576-85-9 6-chloro-2-(4-methyl-piperazin-1-yl)-4-phenyl-quinoline 
• 31576-83-7 6-chloro-2-morpholin-4-yl-4-phenyl-quinoline 
• 76093-58-8 6-Chloro-4-phenyl-2-piperazin-1-yl-quinoline 
• 31576-98-4 6-Chlor-2-dimethylamino-4-phenylchinolin 

Relevant academic research and scientific papers

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides

Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions

A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is

Lactamization of alkenyl C-H bonds to generate 2-quinolinones with triphosgene

A simple and easy-going method is developed to synthesize the analogues of 2-quinolinones by using triphosgene (BTC) as the carbonyl source. In these reactions, both the toxic carbon monoxide (CO) and phosgene are avoided and the 2-quinolinones are obtained in moderate to good yields under mild conditions, all of which are anticipated to be meaningful in both industry and laboratory.

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

Visible-Light-Induced Decarboxylation Coupling/Intramolecular Cyclization: A One-Pot Synthesis for 4-Aryl-2-quinolinone Derivatives

A visible-light-induced decarboxylation coupling/intramolecular cyclization is reported. The one-pot synthesis system provides mild, efficient, and atom economical access to the synthesis of 4-aryl-2-quinolinone derivatives. It is notable that the necessa

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.

Palladium-catalyzed arylation/cyclization/desulfonation cascades toward 4-aryl quinolin-2(1H)-ones with diaryliodonium salts

Palladium-catalyzed cascades of arylation/cyclization/desulfonation of ortho-aminocinnamate esters by using diaryliodonium salts afforded a wide range of 4-aryl quinolin-2(1H)-ones. As such, the desired 4-aryl quinolin-2(1H)-ones with potential biological activity has been synthesized in the yields of 34–96%.

Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines

A novel rapid synthesis of quinolines from 2-alkenylanilines has been described; the reaction involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate (Boc2O, 2.0 equiv), and a series of tert-butyl quinolin-2-yl carbonate with various functional groups have been synthesized in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.

Synthesis of 4-Aryl-2-Quinolones via Copper-Catalyzed Hydroarylation of (o-Aminophenyl)propiolates with Arylboronates

4-Aryl-2(1H)-quinolones were efficiently synthesized via copper-catalyzed hydroarylation of (o-aminophenyl)propiolates with arylboronic acid neopentyl glycol esters. The substrate propiolates were prepared from the corresponding silylalkynes with carbon d

Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols

A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)- 2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N-Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO 4] or the 3-iodo-2-quinolinone (with I2 and H +).