54197-64-7

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is used as an intermediate in the synthesis of pharmaceuticals and fine chemicals for its potential pharmacological properties.
Used in Antimicrobial Applications:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is used as an antimicrobial agent, exhibiting activity against various microorganisms, which makes it a valuable compound in the development of new antimicrobial drugs.
Used in Anti-inflammatory Applications:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is used as an anti-inflammatory agent, demonstrating the ability to reduce inflammation, which can be beneficial in the treatment of various inflammatory conditions.
Used in Diabetic Complications Management:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is studied for its potential as an inhibitor of aldose reductase, an enzyme involved in diabetic complications. Its use as an aldose reductase inhibitor could help in managing and treating complications associated with diabetes.

InChI:InChI=1/C10H11NO2/c1-13-8-3-4-9-7(6-8)2-5-10(12)11-9/h3-4,6H,2,5H2,1H3,(H,11,12)

Upstream product

• 54197-66-9 3,4-dihydro-6-hydroxy-2(1H)-quinolinone 
• 74-88-4 methyl iodide 
• 10226-40-1 5-methoxy-2-nitrocinnamic acid 
• 113961-91-4 1-Hydroxy-6-methoxy-3,4-dihydroquinolin-2(1H)-one 
• 140-88-5 ethyl acrylate 
• 191348-14-8 2-iodo-4-methoxylaniline 
• 1536478-38-2 N-(4-methoxy-2-vinylphenyl)formamide 
• 1536478-81-5 N-(2-bromo-4-methoxyphenyl)formamide 
• 75-03-6 ethyl iodide 
• 201230-82-2 carbon monoxide 
• 126759-31-7 2-vinyl-4-methoxynitrobenzene 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 67363-26-2 3-(4-methoxyphenyl)propanohydroxamic acid 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 

Downstream Products

• 1215765-65-3 1-(4-methoxybenzyl)-3,4-dihydro-6-methoxyquinolin-2(1H)-one 
• 120-15-0 6-methoxy-1,2,3,4-tetrahydroquinoline 
• 91957-45-8 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one 
• 1217436-63-9 6-methoxy-1-(3-phenylprop-2-ynyl)-3,4-dihydroquinolin-2-(1H)-one 
• 115706-38-2 2-(1,2,3,4-tetrahydro-2-oxo-6-methoxyquinolin-1-yl)propionic acid 

Relevant academic research and scientific papers

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)?H Amidation

Benzofused lactams, especially indolin-2-one and dihydroquinolin-2-one are popular structural motives in durgs and natural products. Herein, we developed a room temperature and robust synthesis of benzofused lactams through cobalt(III)-catalyzed C(sp

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates

x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

METHOD FOR PRODUCING LACTAM COMPOUND, AND LACTAM COMPOUND PRODUCED THEREBY

The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones

A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck-Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines as substrates, the one-pot tandem process was extended for the direct synthesis of 3,4-dihydroquinolin-2-ones. In this case, following diazotization and Heck-Matsuda coupling to give methyl cinnamates, addition of hydrogen and reutilization of the palladium catalyst for reduction of the nitro group and hydrogenation of the alkene resulted in efficient formation of 3,4-dihydroquinolin-2-ones. The synthetic utility of this one-pot, four-stage process was demonstrated with the five-pot synthesis of a quinolinone-based sodium ion channel modulator.

Enabling CO Insertion into o-Nitrostyrenes beyond Reduction for Selective Access to Indolin-2-one and Dihydroquinolin-2-one Derivatives

The transition metal-catalyzed reductive cyclization of o-nitrostyrene in the presence of carbon monoxide (CO) has been developed to be a general synthetic route to an indole skeleton, wherein CO was used as a reductant to deoxidize nitroarene into nitrosoarene and/or nitrene with CO2 release, but the selective insertion of CO into the heterocyclic product with higher atom economy has not yet been realized. Herein, the Pd-catalyzed reduction of o-nitrostyrene by CO and its regioselective insertion were efficiently achieved to produce synthetically useful five- and six-membered benzo-fused lactams. Detailed investigations revealed that the chemoselectivity to indole or lactam was sensitive to the nature of the counteranions of Pd2+ precursors, whereas ligands significantly decided the carbonylative regioselectivity by different reaction pathways. Using PdCl2/PPh3/B(OH)3 (condition A), an olefin hydrocarboxylation was primarily initiated followed by partial reduction of the NO2 moiety and cyclization reaction to give N-hydroxyl indolin-2-one, which was further catalytically reduced by CO to afford the indolin-2-one as the final product with up to 95% yield. When the reaction was conducted under the Pd(TFA)2/BINAP/TsOH·H2O system (condition B), complete deoxygenation and carbonylation of the NO2 group occurred initially to yield the corresponding isocyanate followed by internal hydrocyclization to generate 3,4-dihydroquinolin-2-one with up to 98% yield. Importantly, the methodology could be efficiently applied in the synthesis of marketed drug Aripiprazole.

Pyrimidine heterocyclic compounds, preparation method and application thereof

The present invention relates to compounds of a formula (I) shown in the description, and pharmaceutically acceptable salts, prodrugs and solvates thereof, and the compounds are useful for treating cancer and inflammation in mammals. The invention also discloses a preparation method for the compounds of the formula (I) and a pharmaceutical composition containing the compound.

Biocatalytic α-Oxidation of Cyclic Amines and N-Methylanilines for the Synthesis of Lactams and Formamides

An environmentally friendly method for the synthesis of lactams and formamides through the biocatalytic α-oxidation of amines was developed by employing Pseudomonas plecoglossicida ZMU-T04 as a biocatalyst. In this biocatalytic process, the α-oxidation of cyclic amines and N-methylanilines proceeded smoothly to give the corresponding amides in low to high yields. Furthermore, it was demonstrated that synthetic 3,4-dihydroquinolin-2(1H)-one could be used as a key precursor of antidepressant bioactive molecules. The mechanism of this biocatalytic α-oxidation process was investigated by isotope- labeling experiments.

IMIDAZOLE COMPOUNDS AS MODULATORS OF FSHR AND USES THEREOF

The present invention relates to imidazole compounds, and pharmaceutically acceptable compositions thereof, useful as positive allosteric modulators of follicle stimulating hormone receptor (FSHR).