67176-93-6

Usage

Synonyms

Phenyl-3,4-dihydro-1(2H)-quinolinone

Type of compound

Heterocyclic compound

Backbone structure

Quinoline

Substituent

Phenyl group

Applications

+ Pharmaceuticals (intermediate in the synthesis of various drugs)
+ Agrochemicals
+ Synthetic organic chemistry

Biological activity

Inhibitor of amyloid β-protein aggregation (associated with Alzheimer's disease)

Potential use

Antitumor agent

Upstream product

• 65690-71-3 N-(1-phenylpropionyl)-N-phenylhydroxylamine 
• 7647-01-0 hydrogenchloride 
• 108-86-1 bromobenzene 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 1069137-61-6 1-chloro-3,4-dihydroquinolin-2(1H)-one 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 79-06-1 2-propenamide 
• 3271-81-6 hydrocinnamanilide 
• 62-53-3 aniline 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 3297-76-5 1-phenyl-1,2,3,4-tetrahydroquinoline 
• 792122-66-8 3-(2-chloro-ethyl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 792122-64-6 3-(3-chloro-propyl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 792122-63-5 3-ethyl-1-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 792122-71-5 1-phenyl-3-propyl-3,4-dihydro-1H-quinolin-2-one 
• 792122-32-8 3-(2-methylamino-ethyl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 868701-18-2 3-(3-hydroxy-propyl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 792122-30-6 3-(3-methylamino-propyl)-1-phenyl-3,4-dihydro-1H quinolin-2-one 
• 792122-36-2 3-(3-methylamino-propyl)-1-phenyl-3-propyl-3,4-dihydro-1H-quinolin-2-one 
• 142338-31-6 3,4-dihydro-3-methyl-1-phenyl-quinolin-2(1H)-one 

Relevant academic research and scientific papers

NIS-mediated oxidative arene C(sp2)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives

A new radical-mediated intramolecular arene C(sp2)-H amidation of 3-phenylpropanamides or [1,1′-biphenyl]-2-carboxamides was developed to prepare a series of 3,4-dihydro-2(1H)-quinolinone and phenanthridone derivatives in moderate to excellent yields (33-94%). Spirolactams could also be obtained using this protocol.

Multicomponent multicatalyst reactions (MC)2R: One-pot synthesis of 3,4-dihydroquinolinones

A Rh/Pd/Cu catalyst system led to an efficient synthesis of dihydroquinolinones in one-pot, two operations. The reaction features the first triple metal-catalyzed transformations in one reaction vessel, without any intermediate workup. The conjugate-addition/amidation/amidation reaction sequence is highly modular, divergent, and practical.

Aryl halide tolerated electrophilic amination of arylboronic acids with N-chloroamides catalyzed by CuCl at room temperature

(Chemical Equation Presented) N-Cl is no competition: Aryl halides were tolerated in an efficient ligandless CuCl-catalyzed electrophilic amination reaction of arylboronic acids with N-chloroamides (see scheme; Ac=acetoxy). This coupling proceeded smoothly at ambient temperature, and products were obtained with good to excellent yields.

1-Aryl-3,4-dihydro-1H-quinolin-2-one derivatives, novel and selective norepinephrine reuptake inhibitors

A novel series of 1-aryl-3,4-dihydro-1H-quinolin-2-ones have been discovered as potent and selective norepinephrine reuptake inhibitors. Efficient synthetic routes have been developed which allow for the multi-gram preparation of both final targets and ad

TREATMENT OF LEARNING DISABILITIES AND MOTOR SKILLS DISORDER WITH NOREPINEPHRINE REUPTAKE INHIBITORS

Provided are methods and medicaments for treating a learning disability or a Motor Skills Disorder, comprising administering to a patient in need of such treatment an effective amount of a selective norepinephrine reuptake inhibitor.

TREATMENT OF PERVASIVE DEVELOPMENTAL DISORDERS WITH NOREPINEPHRINE REUPTAKE INHIBITORS

Provided are methods and medicaments for treating a Pervasive Developmental Disorder, comprising administering to a patient in need of such treatment an effective amount of a selective norepinephrine reuptake inhibitor.

TREATMENT OF HOT FLASHES, IMPULSE CONTROL DISORDERS AND PERSONALITY CHANGE DUE TO A GENERAL MEDICAL CONDITION

Selective norepinephrine reuptake inhibitors are useful for the prevention or treatment of hot flashes, vasomotor symptoms, impulse control disorders or personality change due to a general medical condition.

QUINOLONE DERIVATIVES

This invention relates to compounds of formula (I) where -X-, n, R1, R3 and Ar- have the values defined herein, their preparation and use as norepinephrine reuptake inhibitors useful for the treatment of nervous system disorders

Microwave-enhanced Goldberg reaction: A novel route to N-arylpiperazinones and N-arylpiperazinediones

An unprecedented microwave-enhanced Goldberg reaction constitutes the key strategic step in the synthesis of N-arylpiperazinones, N-arylpiperazinediones and N-aryl-3,4-dihydroquinolinones. Microwave irradiation greatly accelerates the Goldberg reaction using NMP as solvent. Alkylation at the 3-position of the formed N-aryl-2-piperazinones furnishes new N-aryl-3-alkyl-2-piperazinones.

A REVISED STRUCTURE FOR THE PRODUCT OF THE ACID CATALYZED REARRANGEMENT OF N-(1-PHENYLPROPIONYL)-N-PHENYLHYDROXYLAMINE

The reaction of N-(1-phenylpropionyl)-N-phenylhydroxylamine 2 with trifluoromethanesulphonic acid at 80 deg C gives the 1-phenyl-1,2,3,4-tetrahydoquinolin-2-one 3.For this compound a 5,6,7,8-tetrahydro-dibenzazocin-6-one 1 has been previously reporte