20150-83-8

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-6-methyl-2(1H)-quinolinone is used as an antimalarial agent for treating malaria caused by Plasmodium parasites. Its chemical structure allows it to target and inhibit essential processes in the parasite's life cycle, thereby reducing the disease's impact on human health.
3,4-Dihydro-6-methyl-2(1H)-quinolinone is also used as an antitumor agent in cancer treatment. Its potential to interfere with cancer cell growth and proliferation makes it a candidate for further research and development in oncology.
Used in Antimicrobial Applications:
In the field of antimicrobials, 3,4-dihydro-6-methyl-2(1H)-quinolinone is used as an antifungal agent to combat fungal infections. Its ability to target fungal cells and inhibit their growth can contribute to the development of new antifungal drugs.
3,4-Dihydro-6-methyl-2(1H)-quinolinone is used as an antibacterial agent to fight bacterial infections. Its potential to disrupt bacterial cell functions and inhibit their growth can lead to the creation of new antibiotics to address antibiotic-resistant bacteria.
Used in Antioxidant Formulations:
3,4-Dihydro-6-methyl-2(1H)-quinolinone is used as an antioxidant in various formulations to protect against oxidative stress and damage. Its capacity to neutralize free radicals and reactive oxygen species can contribute to the development of antioxidant therapies and supplements.
Used in Organic Synthesis:
In the field of organic synthesis, 3,4-dihydro-6-methyl-2(1H)-quinolinone is used as a building block for the synthesis of various organic compounds and pharmaceutical drugs. Its unique chemical structure allows it to be a versatile component in the creation of new molecules with potential applications in medicine, agriculture, and other industries.

Upstream product

• 4053-34-3 6-methylquinolin-2(1H)-one 
• 113961-90-3 1-hydroxy-6-methyl-1,2,3,4-tetrahydroquinolin-2-one 
• 7446-70-0 aluminium trichloride 
• 19342-88-2 3-chloro-N-(4-methylphenyl)propionamide 
• 106-49-0 p-toluidine 
• 29289-13-2 2-iodo-4-methylaniline 
• 140-88-5 ethyl acrylate 
• 107-18-6 allyl alcohol 
• 3751-48-2 3-(3-methylphenyl)propanoic acid 
• 103040-39-7 3-(3-methylphenyl)propionyl chloride 
• 58183-40-7 3-(p-tolyl)propionyl chloride 
• 1251303-74-8 C₁₀H₁₃NO₂ 
• 1505-50-6 3-(4-Methylphenyl)propanoic acid 
• 578-46-1 5-methyl-2-nitroaniline 

Downstream Products

• 91-61-2 6-methyl-1,2,3,4 tetrahydroquinoline 
• 194979-95-8 4,8-dimethyl-2,3,5,6-tetrahydro-(1H)-benzo[c]quinolizin-3-one 
• 871269-46-4 (Z)-3-(1-acetylamino-1-phenylmethylene)-1,5-dimethyl-3,4-dihydroquinolin-2(1H)-one 

Relevant academic research and scientific papers

A Four-Component Cascade C-H Functionalization/Cyclization/Nucleophilic Substitution Reaction to Construct α-Functionalized Tetrahydroquinolines by the Strategy of in Situ Directing Group Formation

A four-component cascade C-H functionalization/cyclization/nucleophilic substitution reactions of anilines, carboxylic anhydrides, propenol, and alkohols have been developed by a strategy of in situ directing group formation, affording an efficient and convenient synthesis of α-alkoxyl tetrahydroquinolines from basic starting materials. A plausible mechanism involving rhodium(III) catalytic C-H functionalization and double nucleophilic attacks is proposed. The nucleophilicity order of some alcohols is also obtained for the cascade reaction.

Dehydrogenative and Redox-Neutral N-Heterocyclization of Aminoalcohols Catalyzed by Manganese Pincer Complexes

A new manganese catalyzed heterocyclization of aminoalcohols has been accomplished. A wide range of heterocycles were synthesized, including 1,2,3,4-tetrahydroquinolines, dihydroquinolinones, and 2,3,4,5-tetrahydro-1H-benzo[b]azepines. The reaction is performed under mild reaction conditions using air and moisture stable manganese catalysts. The desired heterocycles were obtained in good to excellent yields.

Discovery of tetrahydroquinolines and benzomorpholines as novel potent RORγt agonists

The retinoic acid receptor-related orphan receptor γt (RORγt) is an important nuclear receptor that regulates the differentiation of Th17 cells and production of interleukin 17(IL-17). RORγt agonists increase basal activity of RORγt and could provide a potential approach to cancer immunotherapy. Herein, hit compound 1 was identified as a weak RORγt agonist during in-house library screening. Changes in LHS core of 1 led to the identification of tetrahydroquinoline compound 6 as a partial RORγt agonist (max. act. = 39.3%). Detailed structure-activity relationship on substituent of the LHS core, amide linker and RHS arylsulfonyl moiety was explored and a novel series of tetrahydroquinolines and benzomorpholines was discovered as potent RORγt agonists. Tetrahydroquinoline compound 8g (EC50 = 8.9 ± 0.4 nM, max. act. = 104.5%) and benzomorpholine compound 9g (EC50 = 7.5 ± 0.6 nM, max. act. = 105.8%) were representative compounds with high RORγt agonistic activity in dual FRET assay, and they showed good activity in cell-based Gal4 reporter gene assay and Th17 cell differentiation assay (104.5% activation at 300 nM of 8g; 59.4% activation at 300 nM of 9g). The binding modes of 8g and 9g as well as the two RORγt inverse agonists accidentally discovered were also discussed.

Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover

We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.

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.