2311-82-2

Upstream product

• 736-03-8 diethyl mesoxalate methyl(phenyl)hydrazone 
• 609-09-6 Diethyl ketomalonate 
• 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 
• 95-54-5 1,2-diamino-benzene 
• 186581-53-3 diazomethane 

Downstream Products

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

Relevant academic research and scientific papers

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.

Metal-free C3-alkoxycarbonylation of quinoxalin-2(1H)-ones with carbazates as ecofriendly ester sources

Quinoxaline-3-carboxylates and analogues are prevalent key structural motifs in bioactive natural products and synthetic drugs. However, the practical protocol for preparation of these motifs from simple raw materials under mild conditions remains rare. In this article, we report a facile protocol for the efficient preparation of various quinoxaline-3-carbonyl compounds (30 examples, 63%–92%) through oxidation coupling of quinoxalin-2(1H)-ones with readily available carbazates (or acyl hydrazines) in the presence of K2S2O8 as an oxidant in metal- and base-free conditions. When tert-butyl carbazate was used as the coupling reagent, the decarboxylation product 3-(tert-butyl)-1-methylquinoxalin-2(1H)-one was obtained. The application of this process into a gram-scale synthesis can be easily accomplished. Mechanistic investigations reveal that the functionalization of quinoxalin-2 (1H)-ones via a free-radical pathway.

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.

Ligand-free Pd(II)-catalyzed cyclization of α-chloroimino-N-arylamides to synthesis of quinoxalin-2(1H)-ones

A ligand-free Pd(II)-catalyzed synthesis of quinoxalin-2(1H)-ones has been developed. Pd(TFA)2 can induce ethyl 2-(N-arylcarbamoyl)-2-chloroiminoacetates to undergo cyclization to afford quinoxalin-2(1H)-one products in high yields in the presence of Na2CO3. This catalytic system is also effective to convert α-aryl-α-chloroimino-N-arylamides to the corresponding quinoxalin-2(1H)-one products via tandem N-Cl cleavage and N-arylation in moderate yields. The reaction described herein constitutes simple and effective approach towards quinoxalin-2(1H)-one derivatives.

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

Visible Light-Induced Radical Cyclization of Ethyl 2-(N-Arylcarbamoyl)-2-Chloroiminoacetates: Synthesis of Quinoxalin-2(1H)-ones

This paper reveals that visible light irradiation with Ru(phen)3Cl2 as photocatalyst can induce ethyl 2-(N-arylcarbamoyl)-2-chloroiminoacetates to undergo NCl cleavage to give α-(aminocarbonyl)iminyl radicals under an argon atmosphere. The subsequent cyclization of the thus formed iminyl radicals affords quinoxalin-2(1H)-one products in good yield in the presence of an inorganic base such as Na2CO3. The reactions proceeded very well even without using a photocatalyst when DMF was used as the solvent. These protocols provide a new, simple method for the generation of iminyl radicals, and the reactions described herein constitute an efficient method for the synthesis of quinoxalin-2(1H)-one derivatives.

OXOPYRAZINE DERIVATIVE AND HERBICIDE

The present invention is to provide an oxopyrazine derivative having an excellent herbicidal activity and besides exhibiting high safety for useful crops and the like , or a salt thereof, and a herbicide containing the same. The present invention relates

REARRANGEMENTS OF AROMATIC CARBONYL ARYLHYDRAZONES OF BENZENE, NAPHTHALENE, AND AZULENE

Aromatic carbonyl arylhydrazones have been shown to undergo two kinds of rearrangement in polyphosphoric acid both involving nitrogen-nitrogen bond cleavage.The first proceeds via insertion of the imine portion in the position ortho to the second nitrogen atom to give o-phenylenediamine intermediates: their evolution depends on the nature of the starting substrate.This reaction has been employed for synthesizing the quinoxalines (5) and the phenanthridines (11), and was demonstrated to be intramolecular.The second reaction path is a sigmatropic rearrangment exclusive to electron-rich aromatic carbonyl hydrazones.