132346-18-0

Upstream product

• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 1029963-89-0 3-phenyl-2-azido-N-(2-iodophenyl)-N-methylpropanamide 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 100-39-0 benzyl bromide 
• 87100-28-5 pinacol benzylboronate 
• 4463-42-7 benzyl boronic acid 
• 94-36-0 dibenzoyl peroxide 
• 1539-57-7 diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 108-88-3 toluene 
• 95-54-5 1,2-diamino-benzene 
• 5416-07-9 3-phenyl-2-thioxopropanoic acid 
• 24949-43-7 3-benzylquinoxalin-2-one 

Relevant academic research and scientific papers

Synthesis method and application of photocatalytic C-3 alkyl-substituted quinoxalin-2(1H)-one compound

The invention relates to the technical field of synthetic methods of quinoxalin-2(1H)-one compounds, in particular to a synthetic method and application of a photocatalytic C-3 alkyl-substituted quinoxalin-2(1H)-one compound. According to the invention, the C-3 alkyl-substituted quinoxalin-2(1H)-one compound is synthesized by using quinoxalin-2(1H)-one, a derivative thereof and substituted sulfonium salt as raw materials, an organic photosensitizer as a photocatalyst, at least one carbonate or nitrogen-containing organic alkali as alkali in an inert gas environment and under the condition of normal temperature and adopting near-blue light to irradiate reaction liquid. The synthesis method disclosed by the invention is simple in preparation process and device, adopts near-blue light as energy, is mild in reaction conditions, and is green and environment-friendly; and the synthesis method is direct alkylation at the C-3 site, and complex pretreatment is not needed, so the method accords with the environmental protection concepts of green chemistry and atom economy.

Direct functionalization of quinoxalin-2(1H)-one with alkanes: C(sp2)-H/C(sp3)-H cross coupling in transition metal-free mode

Considering the significance of pharmaceutically important heterocycles, efficient and highly versatile protocols for the functionalization of diverse heterocycles with easily accessible feedstock are crucial. Here, we have reported selective alkylation of quinoxalin-2(1H)-one with a broad class of hydrocarbons having different C(sp3)-H bonds with varying bond strengths using di-tert-butyl peroxide (DTBP) as an alkoxyl radical mediator for hydrogen atom transfer (HAT). This dehydrogenative coupling approach utilizes feedstock chemicals such as cycloalkanes, cyclic ethers and alkyl arenes as coupling partners. This protocol exhibits good functional group compatibility and selectivity regarding both heterocycles and unactivated alkanes. Moreover, this methodology allows functionalization of relatively strong C-H bonds of adamantane and exclusive selectivity towards 3° C(sp3)-H bonds is observed. We also illustrate the applicability of this C(sp2)-H/C(sp3)-H cross-coupling for practical access to bioactive pharmaceuticals.

Method for preparing benzylated quinoxalinone compound under visible light catalysis

The invention discloses a method for preparing a benzylated quinoxalinone compound under visible light catalysis. The benzylated quinoxalinone compound is synthesized under the irradiation of visible light by taking a quinoxalinone compound and benzyl bromide as raw materials, xanthate as a catalyst and sodium acetate (NaOAc) as an additive. The method has the advantages of mild reaction conditions, simplicity and convenience in operation, no oxidant, wide substrate application range and the like. The compound has potential application value in the research fields of medicine, organic synthesis and the like, can be used for synthesizing a drug molecule, namely an aldose reductase inhibitor and a structural molecule with anti-depression activity, and provides a new preparation method for synthesis of benzylquinoxalinone compounds.

Visible-light-induced chemoselective reactions of quinoxalin-2(1H)-ones with alkylboronic acids under air/N2 atmosphere

A visible-light-induced chemoselective reactions of quinoxalin-2(1H)-ones with alkylboronic acids in the presence of air (O2) and N2 atmosphere was developed under transition-metal free conditions, providing 3-alkylquinoxalin-2(1H)-ones and 3,4-dihydroquinoxalin-2(1H)-ones, respectively. The overall strategy accommodates a broad scope of substituted quinoxalin-2(1H)-ones and alkylboronic acids with good to excellent product yields.

BI-OAc-Accelerated C3-H Alkylation of Quinoxalin-2(1 H)-ones under Visible-Light Irradiation

An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to und

Green synthesis method 1 -methyl -3 -alkyl quinoxalinone compound (by machine translation)

The invention discloses a green synthesis method 1 -methyl -3 -alkyl quinoxaline ketone compound, wherein 380 - 385 nm methyl quinoxaline ketone compound and a benzoyl peroxide compound are reacted in one pot in a hexafluoroisopropanol solution under 1 -

Copper-Catalyzed Direct C-3 Benzylation of Quinoxalin-2(1H)-ones with Methylarenes under Microwave Irradiation

A novel and efficient approach to the C(sp2)–H/C(sp3)–H oxidative coupling of quinoxalin-2(1H)-ones with methylarenes by using CuI as catalyst is reported. Various substrates were well tolerated in this methodology and the desired products were given in moderate-to-good yields. This reaction features good functional group compatibility and broad substrate scope.

A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments

A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.

Iminyl radicals from α-azido o-iodoanilides via 1,5-H transfer reactions of aryl radicals: New transformation of α-azido acids to decarboxylated nitriles

(Chemical Equation Presented) The radical reaction of tributyltin hydride with o-iodo-N-methylanilides derived from α-azido acids provides an excellent access to α-(aminocarbonyl)iminyl radicals through 1,5-hydrogen transfer reaction of initially formed aryl radicals followed by β-elimination of dinitrogen from ensuing α-azido-α- (aminocarbonyl)alkyl radicals. The outcoming iminyls display a peculiar tendency to form corresponding nitriles by β-elimination of aminocarbonyl radicals.

Structure-activity studies of substituted quinoxalinones as multiple-drug-resistance antagonists

A significant problem in the clinical treatment of cancer relates to the development of tumor resistance to many chemotherapeutic agents. Acquired drug resistance is often mediated through overexpression of membrane transport proteins that effectively efflux anticancer agents. Two of the best-studied transporters, P-glycoprotein (Pgp) and MRP1, have pharmacological properties that only partially overlap. In our search for improved drug-resistance antagonists, we have identified a family of substituted quinoxalines that selectively antagonizes Pgp over MRP1. Consequently, a focused library of congeners was designed and synthesized starting with a parent bromomethylquinoxalinone. This parent quinoxalinone was then condensed with a series of phenols to yield a family of substituted phenoxymethylquinoxalinones. These compounds were evaluated for their toxicity toward drug-sensitive MCF-7 breast carcinoma cells and for their abilities to antagonize Pgp and MRP1 in drug-resistant cell lines (NCI/ADR and MCF-7/VP, respectively). The results of this structure-activity study indicate that compounds with carbonyl substitutions of the phenoxy group (ester, amide, or ketone moieties) demonstrate excellent antagonism of Pgp while having relatively low toxicity toward drug-sensitive cells. Importantly, none of these compounds antagonized MRP1. Because of their transporter selectivity, we predict that substituted quinoxalinones may be more effective MDR modulators in vivo than are nonselective transporter antagonists.