1677-46-9

Usage

Uses

Used in Electrochemical Oxidation:
4-HYDROXY-1-METHYL-2-QUINOLONE is used as a nucleophile in the electrochemical oxidation of catechols. The reaction is studied using techniques such as cyclic voltammetry and controlled-potential coulometry, which help in understanding the reaction mechanism and optimizing the process for various applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-HYDROXY-1-METHYL-2-QUINOLONE serves as a key intermediate for the synthesis of various complex molecules. It is used in the ceric ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds, yielding substituted dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, and dihydrofurophenalenones. These synthesized compounds find applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
4-HYDROXY-1-METHYL-2-QUINOLONE is used as a building block in the synthesis of various pharmaceutical compounds. Some examples include 3-(4-methoxybenzyl)-4-hydroxy-1-methylquinolinone, 3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-hydroxy-1-methylquinolin-2(1H)-one, 3-(4-chlorobenzyl)-4-hydroxy-1-methylquinolin-2(1H)-one, and 3,3′-bis(4-chlorobenzylidene)-1,10-methylquinolin-2,20-(1H)-one. These synthesized compounds may exhibit biological activities such as antimicrobial, anti-inflammatory, or other therapeutic properties, making them valuable in the development of new drugs.
Used in Chemical Research:
4-HYDROXY-1-METHYL-2-QUINOLONE is also utilized in academic and industrial research settings for the development of new synthetic methods, understanding reaction mechanisms, and exploring the potential of quinolone-based compounds in various applications, including materials science, catalysis, and environmental remediation.

InChI:InChI=1/C10H9NO2/c1-11-8-5-3-2-4-7(8)9(12)6-10(11)13/h2-6,12H,1H3

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 115-18-4 2-methyl-3-buten-2-ol 
• 152628-30-3 3-Iod-N-methyl-4-tosyloxy-chinolin-2(1H)-on 
• 60657-74-1 3-(methyl(phenyl)amino)-3-oxopropanoic acid 
• 146828-46-8 1-methyl-2,4-dioxo-quinoline-3-carboxylic acid 
• 90061-40-8 3-Brom-4-hydroxy-1-methyl-1,2-dihydrochinolin-2-on 
• 98751-17-8 4-hydroxy-3-iodo-1-methyl-1,2-dihydroquinolin-2-one 
• 57513-54-9 ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 10328-92-4 N-Methylisatoic anhydride 
• 54289-76-8 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone 
• 2922-83-0 L-kynurenine 
• 485-80-3 S-adenosyl-L-methionine 

Downstream Products

• 32262-17-2 4-chloro-1-methyl-1H-quinolin-2-one 
• 703-61-7 2,4-dichloroquinoline 
• 40335-01-1 2-methoxy-1-methyl-1H-quinolin-4-one 
• 32262-18-3 N-methyl-4-methoxyquinolin-2(1H)-one 
• 96600-76-9 4-Chloro-3-formyl-1-methyl-2(1H)-quinolinone 
• 110229-40-8 4-(p-toluenesulfonyloxy)-1-methyl-quinolin-2(1H)-one 
• 96600-77-0 2-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)cyclohexa-2,5-diene-1,4-dione 
• 181937-81-5 2-Methyl-benzoic acid 1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester 
• 211686-36-1 4-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one 
• 211686-40-7 3-cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one 

Relevant academic research and scientific papers

Synthesis of new quinolinones from 3-nitropyranoquinolinones

Alkaline hydrolysis of 3-nitropyranoquinolinones (6-alkyl-4-hydroxy-3-nitro-2H-pyrano[3,2-c]quinoline-2,5(6H)-diones) for different reaction times gave five products which were formed by the progressive degradation of the nitropyrano ring. Varying amounts of 3-nitroacetylquinolinones, quinolinones with side-chains of β- And β-ketoacids, quinolinone-3-carboxylic acids and 4-hydroxyquinolinones were isolated. With the aim of preparing new biologically active quinolone derivatives, the products of reaction of the 3-nitropyranoquinolinones with side-chains of α- And β-ketoacids with some nitrogen and carbon nucleophiles were also studied, some giving rise to annulated products.

Enzymatic formation of quinolone alkaloids by a plant type III polyketide synthase

(Chemical Equation Presented) Benzalacetone synthase from Rheum palmatum efficiently catalyzed condensation of N-methylanthraniloyl-CoA (or anthraniloyl-CoA) with malonyl-CoA (or methylmalonyl-CoA) to produce 4-hydroxy-2(1H)-quinolones, a novel alkaloidal scaffold produced by a type III polyketide synthase (PKS). Manipulation of the functionally divergent type III PKSs by a nonphysiological substrate thus provides an efficient method for production of pharmaceutically important quinolone alkaloids.

Substituted quinolinones. Part 19. New and unexpected results from oxidation of 3-acetyl-1-alkyl- 4-hydroxyquinolin-2(1H)-ones using selenium dioxide

Oxidation of 3-acetyl-1-alkyl-4-hydroxyquinolin-2(1H)-ones using selenium dioxide under Riley conditions was described. The oxidation reaction produced a mixture of 2 unexpected α-keto acid and its dehydrated dimer derivatives. The oxidation reaction was studied under different reaction conditions in order to maximize the yields and optimize reaction conditions. Also, 1-alkyl-4-hydroxy-3-(2-nitroacetyl)quinolin-2(1H)-one and/or 3-acetyl-1-alkyl-4-diflouro-boryloxyquinolin-2(1H)-one derivatives were subjected to the same oxidation reaction giving rise improved reaction yields and selectivity in case of the boron-complex. Alkaline degradation of the dehydrated dimers led to formation of the 4-hydroxy-2-oxoquinoline-3-carboxylic acids while under the same conditions the α-keto acids underwent deoxalylation.

Methylation of 4-Hydroxy-2-quinolone

The reaction of 4-hydroxy-2-quinolone (1a) with methyl iodide/potassium hydroxide in boiling acetone gave a mixture of 1-methyl-4-methoxy-2-quinolone (1d), 1,3-dimethyl-4-methoxy-2-quinolone (1e), and 1,3,3-trimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline (2).As by-product 2,4-dimethoxyquinoline (3) was identified.Under the same conditions 4-methoxy-2-quinolone (1c) yielded 1d, 1e, 2 and 3, while 1-methyl-4-hydroxy-2-quinolone (1b) gave 1d, 1e and 2.

BACTERIOSTATIC HETEROCYCLES FROM EUODIA LUNU-ANKENDA

A new constituent characterized as 8-acetyl-3,4-dihydroxy-5,7-dimethoxy-2,2-dimethylchroman has been isolated together with alloevodionol-7-methyl ether, 4-methoxy-1-methyl-2(1H) quinolinone, evolitrine, isoevodionol and its methyl ether from the aerial parts of Euodia lunu-ankenda.Its structure was confirmed by its transformation to alloevodionol-7-methyl ether. 4-Methoxy-1-methyl-2(1H)quinolinone and its isomer were synthesized by a modified procedure.Key Word Index - Euodia lunu-ankenda; Rutaceae; 8-acetyl-3,4-dihydroxy-5,7-dimethoxy-2,2-dimethylchroman; alloevodionol-7-methyl ether; 4-methoxy-1-methyl-2(1H)quinolinone; isoevodionol; isoevodionol methyl ether; antibacterial activity.

Rapid preparation of pyranoquinolines using microwave dielectric heating in combination with fractional product distillation

4-Hydroxy-6-methyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione was prepared by microwave-assisted cyclocondensation of N-methylaniline with 2 equiv of diethyl malonate. Key to the success of the synthesis was the use of open vessel controlled microwave heating technology, allowing the simultaneous removal of the formed ethanol from the reaction mixture by fractional distillation.

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.

Engineered Biosynthesis of Fungal 4-Quinolone Natural Products

Quinolone-containing natural products are widely found in bacteria, fungi, and plants. The fungal quinolactacins, which are N-methyl-4-quinolones, display a wide spectrum of biological activities. Here we uncovered a concise nonribosomal peptide synthetase pathway involved in quinolactacin A biosynthesis from Penicillium by using heterologous reconstitution and in vitro enzymatic synthesis. The N-desmethyl analog of quinolactacin A was accessed through the construction of a hybrid bacterial and fungi pathway in the heterologous host.

Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors

Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRF-CEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50 = 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds’ activity.