28563-18-0

Usage

Classification

Quinolinone compound

Functional groups

Chlorine atom, hydroxyl group, phenyl group

Pharmacological activities

Potential use as an antitumor agent, ability to inhibit cancer cell growth, anti-inflammatory and antioxidant properties

Potential applications

Development of novel pharmaceuticals and medicinal products

InChI:InChI=1/C15H10ClNO2/c16-10-6-7-12-11(8-10)14(18)13(15(19)17-12)9-4-2-1-3-5-9/h1-8H,(H2,17,18,19)

Upstream product

• 106-47-8 4-chloro-aniline 
• 83-13-6 diethyl 2-phenylmalonate 
• 63069-48-7 p-chloro-o-iodoaniline 
• 536-74-3 phenylacetylene 
• 928782-97-2 4-chloro-2-(phenylethynyl)aniline 
• 124-38-9 carbon dioxide 
• 144603-86-1 N¹,N³-bis(4-chlorophenyl)-2-phenylmalonamide 

Downstream Products

• 1610555-85-5 4-butoxy-6-chloro-3-phenyl-2(1H)-quinolinone 

Relevant academic research and scientific papers

Cu(i)-catalyzed chemical fixation of CO2 with 2-alkynylaniline into 4-hydroxyquinolin-2(1H)-one

A copper(i) catalyzed reaction of 2-alkynylaniline with CO2 using DBU as base to produce 4-hydroxyquinolin-2(1H)-one derivatives in moderate to good yield is presented. In this reaction, a unique bond cleavage pattern for CO2 was observed that one of the C-O double bonds of CO 2 was totally broken and rearranged into two moieties in the absence of the reductive reagent. This efficient reaction system showed the wide generality of substrates including nitro, bromo, cyano and methoxylcarbonyl groups. A possible mechanism containing isocyanate intermediate is proposed. This journal is the Partner Organisations 2014.

Efficient preparation of 4-hydroxyquinolin-2(1 H)-one derivatives with silver-catalyzed carbon dioxide incorporation and intramolecular rearrangement

Although 4-hydroxyquinolin-2(1H)-one derivatives have attracted much attention due to their biological benefits, conventional reactions under harsh heat conditions must be employed to provide these key compounds. In the presence of a catalytic amount of s

Rapid microwave-enhanced synthesis of 4-hydroxyquinolinones under solvent-free conditions

3-Aryl-4-hydroxyquinolin-2(1H)-ones are potent and selective glycine-site NMDA receptor antagonists of pharmaceutical interest. A novel microwave-enhanced synthesis of such quinolinones under solvent-free conditions has been developed. The quinolinones ar

Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange

3-Substituted 4-hydroxy-2(1H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10.Reactions of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11.Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13.Similarly the dichloro quinolinediones 10an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.Keywords.Fluorination; 4-Hydroxy-2(1H)-quinolones, 3-alkyl/3-aryl/3-fluoro; 1-Hydroxy-benzoquinolizine-3-ones, 2-alkyl/3-aryl; Quinoline-2,4(1H,3H)-diones, 3-azido-3-alkyl/3-aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro.