66394-50-1

Usage

Uses

Used in Pharmaceutical Research:
(Z)-3,4-DIHYDRO-3-(2-(4-METHOXYPHENYL)-2-OXOETHYLIDENE)QUINOXALIN-2(1H)-ONE is used as a research compound in the pharmaceutical industry for its potential to contribute to the development of new drugs. Its unique structure and properties allow researchers to explore its possible applications in treating various diseases and disorders.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (Z)-3,4-DIHYDRO-3-(2-(4-METHOXYPHENYL)-2-OXOETHYLIDENE)QUINOXALIN-2(1H)-ONE serves as a key compound for studying its interactions with biological targets. This helps in understanding its potential therapeutic effects and guiding the design of more effective drugs.
Further research and studies are necessary to fully comprehend the capabilities of (Z)-3,4-DIHYDRO-3-(2-(4-METHOXYPHENYL)-2-OXOETHYLIDENE)QUINOXALIN-2(1H)-ONE and to harness its potential in pharmaceutical applications.

InChI:InChI=1/C17H14N2O3/c1-22-12-8-6-11(7-9-12)16(20)10-15-17(21)19-14-5-3-2-4-13(14)18-15/h2-10,18H,1H3,(H,19,21)/b15-10-

Upstream product

• 35322-20-4 ethyl 3-(4-methoxybenzoyl)pyruvate 
• 95-54-5 1,2-diamino-benzene 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 55558-77-5 4-(4-methoxyphenyl)-2,4-dioxobutanoic acid 
• 124928-30-9 Benzoic acid N'-[(Z)-2-hydroxy-4-(4-methoxy-phenyl)-4-oxo-but-2-enoyl]-hydrazide 

Downstream Products

• 389574-76-9 3-(4-methoxy-benzoyl)-5H-pyrrolo[1,2-a]quinoxaline-1,2,4-trione 
• 1006372-87-7 C₁₇H₁₃BF₂N₂O₃ 

Relevant academic research and scientific papers

An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1: H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: Lemon juice as an alternative to hazardous solvents and catalysts

Innovative, efficient, clean, experimentally simple and environmentally friendly one-pot biocatalytic synthesis of two small libraries of 3,4-dihydro-2(1H)-quinoxalinones (4a-m) and 3,4-dihydro-1,4-benzoxazin-2-ones (5a, 5b, 5f and 5k-o) by heterocyclization of ethyl 2-hydroxy-4-alkyl(aryl)-4-oxo-2-butenoates (1a-o) or their corresponding salts (1a′-o′) with o-phenylenediamine (2) or o-aminophenol (3) in lemon juice as a solvent and a catalyst is presented. In all reactions where esters 1a-o are used for 24 h, very good-to-excellent yields were achieved, but the best yield was realized in the synthesis of 5a (97%) from 3 and 1a. The use of enolate salts (1a′-o′) instead of the corresponding esters 1a-o significantly reduced the reaction time (up to 6 h) and good-to-excellent yields were achieved. Groups with electron-donating or -withdrawing effects at the aromatic ring of the ester did not have significant influences on the yield of targeted products. In addition, several selected 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones on a gram-scale in the yields up to 92% were synthesized. The presented synthetic strategy has produced smaller amount of waste without by-products and with excellent values of green chemistry metrics (atom efficiency, reaction mass efficiency, E-factor and EcoScale).

Rapid alkenylation of quinoxalin-2(1H)-ones enabled by the sequential Mannich-type reaction and solar photocatalysis

Herein, a rapid alkenylation of quinoxalin-2(1H)-ones enabled by a combination of Mannich-type reaction and solar photocatalysis is demonstrated. A wide range of functional groups are compatible, affording the corresponding products in moderate-to-good yields. Control experiments illustrate that the in situ generated 1O2 plays a central role in this reaction. This green and efficient strategy provides a practical solution for the synthesis of potentially bioactive compounds that containing a 3,4-dihydroquinoxalin-2(1H)-one structure.

A combination of heterogeneous catalysis and photocatalysis for the olefination of quinoxalin-2(1H)-ones with ketones in water: a green and efficient route to (Z)-enaminones

Herein, a novel aqueous reaction for the olefination of quinoxalin-2(1H)-ones with ketones through a combinational strategy is described. This reaction features very mild conditions using a simple and cheap catalyst for the synthesis of (Z)-enaminones with moderate-to-good yields. Such a methodology successfully combines the heterogeneous Mannich reaction with photocatalysis, and provides a green and practical approach for the synthesis of potentially bioactive (Z)-enaminones with a 3,4-dihydroquinoxalin-2(1H)-one skeleton.

Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxobenzo[1, 4]oxazines and 2-oxoquino[1, 4]oxalines: Synthetic applications, antioxidant activity, SAR and cytotoxic studies

A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1, 4]oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay.

Study on the structureeproperty relationship in a series of novel BF2 chelates with multicolor fluorescence

A series of multicolor fluorescent N,O-bidentate BF2 complexes with variable ligand structures have been synthesized. These complexes exhibit the solvent-independent optical properties and large Stoke shifts. The electrochemical measurements demonstrate that all these chelates are better electron acceptors than the commonly used material Alq3. A qualitative structureeproperty relationship among these complexes has been established on the ground of the experimental data along with the density functional theory (DFT) calculations. The theoretically calculated results are in good agreement with those obtained by the experimental determinations.

The effect of substituents on the response of 3,4-dihydro-3-(2-oxo-2- phenylethylidene)-quinoxalin-2(1H)-one derivatives toward binding of Cu 2+

A new series of fluorogenic chelating reagents based on phenylethylidene-3,4-dihydro-1H-quinoxalin-2-one with different substituents (attached either to the quinoxaline-2-one (3) or phenyl ring (4)) have been investigated to examine the effect of the substituent (nature/position) on the spectral properties and response toward Cu2+ in the presence of other metal cations, in ethanol. It was found that all of the examined ligands exhibit a pronounced response to Cu2+ addition resulting in a red-shift in the UV-vis spectra and a strong quenching in the fluorescence spectra. Among the ligands examined, 3a exhibits the highest selectivity toward various metal cations. In general it appears that the best response selectivity of these ligands toward Cu2+ ion is obtained by either EDG in 3 or EWG in 4. For example, the fluorescence intensity of 3a (with OMe substituent) increases to about three times that of the unsubstituted derivative.

Sulfamic acid as an effective catalyst in solvent-free synthesis of β-enaminoketone derivatives and X-ray crystallography of their representatives

Two types of β-enaminoketone derivatives of 3-(2-oxo-2-arylethylidene) -3,4-dihydro-1H-quinoxalin-2-ones and 3-(2-oxo-2-arylethylidene)-3,4-dihydro- benzo[1,4]oxazin-2- ones were effectively and conveniently prepared in good to excellent yields under solv

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES. XXXV. REACTION OF 5-ARYL-2,3-DIHYDRO-2,3-FURANDIONES WITH KETENE ACETALS. SYNTHESIS, STRUCTURE, AND HETEROCYCLIZATION REACTIONS OF ALKYL 5-ARYL-2-HYDROXY-3-OXO-2,3-DIHYDRO-2-FURYLACETATES

Depending on the nature of the substituent in the benzene ring, in the crystalline state the products from the reaction of 5-aryl-2,3-dihydro-2,3-furandiones with ketene acetals exist in the form of either alkyl 5-aryl-2-hydroxy-3-oxo-2,3-dihydro-2-furyla

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES. XI. SYNTHESIS AND CHEMICAL TRANSFORMATIONS OF THE β-AROYLHYDRAZIDES OF AROYLPYRUVIC ACIDS

The β-aroylhydrazides of aroylpyruvic acids were obtained from 5-aryl-2,3-dihydro-2,3-furandiones and aroylhydrazines.They are cleaved by the action of amines to the β-aroylhydrazides of oxamic acids and by the action of o-phenylenediamine to Z-3-phenacylidene-1,2,3,4-tetrahydro-2-quinoxalones.When treated with hydroxyamine or hydrazines, the β-aroylhydrazides of aroylpyruvic acids form the β-aroylhydrazides of 5-aryl-3-isoxazolecarboxylic and 3-pyrazolecarboxylic acids respectively, which undergo cyclization under the influence of phosphorus oxychloride to 5-aryl-2-(5-aryl-3-isoxazolyl)- and 5-aryl-2-(5-aryl-3-pyrazolyl)-1,3,4-oxidazoles.