85274-64-2

Usage

Chemical compound

6-CHLORO-3-PHENYL-2-QUINOLINOL

Family

Quinolinol

Properties

Contains a chloro group
Contains a phenyl group
Quinolinol ring structure

Pharmacological activities

Anti-inflammatory effects
Anti-bacterial effects

Potential uses

Drug development
Intermediate in pharmaceutical synthesis

Mechanism of action

Interaction with specific targets in the body

Overall significance

Compound of interest for potential pharmacological properties.

InChI:InChI=1/C15H10ClNO/c16-12-6-7-14-11(8-12)9-13(15(18)17-14)10-4-2-1-3-5-10/h1-9H,(H,17,18)

Upstream product

• 94281-62-6 3-Bromo-6-chloro-4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 93696-68-5 2,3-Dibromo-N-(4-chloro-phenyl)-3-phenyl-propionamide 
• 63069-48-7 p-chloro-o-iodoaniline 
• 536-74-3 phenylacetylene 
• 13939-06-5 molybdenum hexacarbonyl 
• 174265-12-4 2-bromo-5-chlorobenzaldehyde 
• 103-81-1 Benzeneacetamide 
• 6277-67-4 4-nitro-1,3-diphenyl-butan-1-one 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 1254211-89-6 C₁₅H₈ClN 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 103-83-3 N,N'-dimethylbenzylamine 

Downstream Products

• 85274-39-1 [2-(6-Chloro-3-phenyl-quinolin-2-ylsulfanyl)-ethyl]-dimethyl-amine 
• 85274-46-0 2,6-dichloro-3-phenylquinoline 

Relevant academic research and scientific papers

Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones

A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.

Palladium-catalyzed carbonylative synthesis of 3-arylquinolin-2(1H)-ones from benzyl chlorides and o-nitrobenzaldehydes

A palladium-catalyzed carbonylative cyclization of benzyl chlorides with o-nitrobenzaldehydes has been developed for the synthesis of 3-arylquinolin-2(1H)-ones. Mo(CO)6 played a dual role as both a CO surrogate and a reductant in this carbonylative transformation.

Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones

An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is

Preparation method of 3-aryl quinoline-2 (1H) ketone derivative

The invention discloses a preparation method of a 3-aryl quinoline-2 (1H) ketone derivative. The method comprises the following steps: carrying out a reaction on palladium acetate, S)-1, 1'-binaphthyl-2, 2'-diphenylphosphine, carbonyl molybdenum, triethylamine, water, benzisoxazole and a benzyl chloride compound at 100 DEG C for 26 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-aryl quinoline-2 (1H) ketone derivative. According to the preparation method, benzisoxazole is used as a nitrogen source and a formyl source, the operation is simple, the reaction initial raw materials are cheap and easy to obtain, the tolerance range of substrate functional groups is wide, and the reaction efficiency is high; and various 3-aryl quinoline-2 (1H) ketone derivatives can be synthesized according to actual needs, and the practicability of the method is widened while the operation is convenient.

Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source

3-Aryl/alkyl-2-quinolones were synthesized employing microwave assisted multicomponent reaction of 2-iodoanilines, terminal alkynes and oxalic acid dihydrate ((CO2H)2 ? 2H2O) under polystyrene supported palladium (Pd@PS) nanoparticles-catalyzed conditions. The use of a heterogeneous palladium catalyst was explored first time for 2-quinolone synthesis involving carbonylation reaction employing (CO2H)2 ? 2H2O as a solid and bench stable carbon monoxide (CO) source. The reaction exhibited good substrate generality for 2-iodoanilines and alkynes with wide functional group tolerance and good regio-selectivity. The ligand free operation, recyclability of heterogeneous Pd@PS catalyst and use of bench stable C1 source are the invaluable merits of the protocol. (Figure presented.).

Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes

A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.

Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.

Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones

A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.

Metal-free transannulation reaction of indoles with nitrostyrenes: A simple practical synthesis of 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.

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.