2311-82-2

Basic information

• Product Name: ethyl 4-methyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate
• CAS NO: 2311-82-2
• Molecular Formula: C₁₂H₁₂N₂O₃
• Molecular Weight: 232.2353
• Mol File: 2311-82-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 363°C at 760 mmHg
• Flash Point: 173.3°C
• Density: 1.26g/cm³
• Vapor Pressure: 1.86E-05mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: ethyl 4-methyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-methyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate(2311-82-2)
• EPA Substance Registry System: ethyl 4-methyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate(2311-82-2)

Safety Data

• Hazardous Substances Data: 2311-82-2(Hazardous Substances Data)

Upstream product

• 685-87-0 Diethyl 2-bromomalonate 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 4114-31-2 ethylhydrazine carboxylate 
• 36818-07-2 ethyl 3-oxo-4H-quinoxaline-2-carboxylate 
• 74-88-4 methyl iodide 
• 609-09-6 Diethyl ketomalonate 
• 95-54-5 1,2-diamino-benzene 
• 736-03-8 diethyl mesoxalate methyl(phenyl)hydrazone 
• 186581-53-3 diazomethane 

Downstream Products

• 18559-42-7 4-methyl-3-oxo-3,4-dihydro-quinoxaline-2-carboxylic acid 

Relevant articles and documents

Synthesis of multisubstituted dihydroquinoxaline derivatives by tandem N-alkylation and addition reactions of 3-oxoquinoxaline-2-carboxylates

This report describes a one-pot synthesis of multisubstituted dihydroquinoxalin-2-ones using an umpolung N-alkylation followed by oxidation and C-alkylation reactions. Moreover, the synthesis of tricyclic compounds containing a dihydroquinoxaline skeleton was carried out by ring closing metathesis (RCM) of the resulting N,C-bis-addition products containing olefins.

Synthesis, EGFR-TK inhibition and anticancer activity of new quinoxaline derivatives

Ethyl 4-substituted-3-oxo-quinoxaline-2-carboxylates 3–5 were obtained via alkylation of ethyl 3-oxo-3,4-dihydroquinoxaline-2-carboxylate (1). Compound 1 was heterocyclized using hydrazines, ethylenediamine, and ethanolamine to give pyrazoloquinoxalines 6, 7, diazepinoquinoxaline 8, and oxazepinoquinoxaline 10. The quinoxaline-2-carboxamides 9, 11, 12 were prepared via condensation of compound 1 with different amines. Compound 1 was thiated using Lawesson’s reagent affording quinoxaline-3-thione 13, in fair yield. In addition, the reaction of 4-methyl-3-oxoquinoxaline 3 with some binucleophiles led to a series of new oxoquinoxaline derivatives 14–18. The molecular structure of compounds 1, 3, and 9 was confirmed by X-ray crystallography. The anti-proliferative activity showed that among all the tested compounds, compounds 3, (IC50 2.51 ± 3.0, 4.22 ± 1.6 and 2.27 ± 1.9 μM), 11 (IC50 1.32 ± 2.61, 1.41 ± 1.23 and 1.18 ± 1.91 μM) and 17 (IC50 1.72 ± 1.32, 1.85 ± 0.94 and 1.92 ± 4.83 μM) showed noteworthy anti-proliferative effects against the three cancer cell lines, HCT116, HePG2 and MCF7, respectively, compared to the reference drugs doxorubicin (IC50 1.41 ± 0.58, 0.90 ± 0.62 and 1.01 ± 3.02 μM) and erlotinib (IC50 1.63 ± 0.81, 1.57 ± 0.62 and 1.49 ± 0.54 μM). Compounds 3 (0.899 nM), 11 (0.508 nM) and 17 (0.807) showed strong EGFR inhibitory activity compared to Erlotinib (0.439 nM) and these results are in agreement with the docking study. These results suggest that compounds could probably be promising anticancer agents with EGFR inhibitory activity.

Tert -Butyl Hypochlorite Induced Cyclization of Ethyl 2-(N -Aryl-carbamoyl)-2-iminoacetates

Ethyl 2-(N -arylcarbamoyl)-2-iminoacetates can be transformed into the corresponding quinoxalin-2-ones in high yield by using the oxidation system of tert -butyl hypochlorite, tetrabutylammonium iodide and tetrabutylammonium chloride. Oxygen exhibits a be