7248-16-0

Usage

Uses

Used in Pharmaceutical Research:
2,3-bis(4-methoxyphenyl)quinoxaline is used as a pharmaceutical candidate for its potential anti-cancer and anti-inflammatory properties. Its structure allows for interactions with biological macromolecules, making it a promising agent for the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3-bis(4-methoxyphenyl)quinoxaline is utilized as a building block for the synthesis of other organic compounds. Its unique structure and chemical properties make it a valuable component in creating a variety of complex organic molecules.

InChI:InChI=1/C22H18N2O2/c1-25-17-11-7-15(8-12-17)21-22(16-9-13-18(26-2)14-10-16)24-20-6-4-3-5-19(20)23-21/h3-14H,1-2H3

Upstream product

• 119-52-8 4,4'-dimethoxybenzoin 
• 95-54-5 1,2-diamino-benzene 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 2213-63-0 2,3-dichloroquinoxaline 
• 5720-07-0 4-methoxyphenylboronic acid 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 637-69-4 4-Methoxystyrene 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 100-66-3 methoxybenzene 
• 88-74-4 2-nitro-aniline 
• 88-67-5 2-Iodobenzoic acid 
• 696-62-8 para-iodoanisole 
• 768-60-5 4-methoxyphenylacetylen 
• 66107-29-7 4-methoxyphenyl triflate 

Downstream Products

• 1075217-51-4 2-butyl-2,3-bis(4-methoxyphenyl)-1H-quinoxaline 
• 863714-59-4 C₈₈H₆₈Cl₂Ir₂N₈O₈ 
• 66679-53-6 2,3-bis-(4-methoxy-phenyl)-quinoxaline 1,4-dioxide 

Relevant academic research and scientific papers

In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature

Substituted quinoxaline derivatives are traditionally synthesized by co-condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o-phenylenediamine and 1,2-diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo-condensation reaction followed by obtaining the aforesaid nitrogen-containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.

Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives

Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to 90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.

Efficient and sustainable Co3O4 nanocages based nickel catalyst: A suitable platform for the synthesis of quinoxaline derivatives

Engineered nanocages have emerged at the forefront of nanomaterial investigation as they possess tremendous potential to boost key chemical processes owing to their hollow architectures that can help in achieving high reactivity. With an intention to make profitable use of their morphological features guided chemical activity, we developed dispersable Co3O4 nanocages decorated with nickel nanoparticles for accessing a broad spectrum of pharmaceutically and biologically active N-heterocyclic quinoxaline nuclei using α-dicarbonyls and 1,2-diamines as precursor reagents. For designing Co3O4 nanocages, we employed a simple and scalable method involving Kirkendall effect in which thermal decomposition of Co3[Co(CN)6]2 was carried out thereafter, nanocages were loaded with Ni nanoparticles to obtain the final Ni@Co3O4 catalyst. Results revealed that Ni@Co3O4 catalyst possesses immense potential to accelerate condensation of diamines and di-carbonyls in absence of any additives under mild reaction conditions. The superior catalytic efficiency has been attributed to the hollow architecture of the nanocatalyst comprising of abundant catalytic sites. This protocol exhibits several remarkable attributes such as mild reaction conditions outstanding functional group tolerance, high yield, immense durability and reusability for six subsequent runs.

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives

In this study, a novel acid-functionalized magnetic nanoparticles with high loaded multifunctional acidic groups was fabricated by anchoring water-soluble 5-sulfosalicylic acid onto the surface silica-modified Fe3O4. The magnetically recyclable Fe3O4@SiO2@5-SA (20?mg) showed excellent reactivity for greener synthesis of tetrahydrobenzo[b]pyrans via a three-component reaction of different aromatic aldehydes, malononitrile and dimedone in good to excellent yields (70–95percent) in pure water at short reaction times (40–150?min). The method shows eco-friendly synthesis of quinoxaline derivatives from direct condensation of substituted 1,2-diamine with various 1,2-dicarbonyl in ethanol at room temperature to afford the desired quinoxalines with good to excellent yields (60–97percent) at shorter reaction times (120–240?min). The morphology and magnetic properties of MNPs were studied with scanning electron microscopy, X-ray powder diffraction, Fourier translation infrared spectroscopy, vibrating sample magnetometer and thermogravimetric. The results showed that the Fe3O4@SiO2@5-SA catalyst is completely recoverable by an external magnet and retained catalytic activity after five recycles.

Dowex 50W: Mild efficient reusable heterogeneous catalyst for synthesis of quinoxaline derivatives in aqueous medium

An efficient, simple and eco-friendly procedure is reported in presence of heterogeneous Dowex 50W catalyst in aqueous medium under refluxing condition to produce quinoxaline derivatives. Catalyst has participated in condensation reaction between 1,2-diamines and various aromatic 1,2-diketones smoothly with excellent yield of the products in short reaction times. Dowex 50W was used more than five times in this reaction separately and showed an excellent recyclability throughout the reaction.(figure presented).

Microwave-Assisted Synthesis of Heterocycles from Aryldiazoacetates**

Herein, we describe a rapid microwave-assisted, metal-free synthesis of substituted quinoxalinones and quinoxalines using the carbene-mediated reaction between aryldiazo esters and 1,2-diamines. The reaction can encompass a range of substituents and structural variations to afford quinoxalin-2-ones in 14–80 % yield and corresponding quinoxalines in good to excellent yields upon oxidation (67–96 %). The approach can be employed to generate symmetrical and unsymmetrical 2,3-diarylquinoxalines, bis-quinoxalines as well as novel quinoxaline-substituted diazo esters and should be a valuable addition to the heterocycle synthesis toolbox.

Synthesis method of quinoxaline heterocyclic derivative

The invention discloses a synthesis method of a quinoxaline heterocyclic derivative. An intermolecular redox reaction and a condensation cyclization reaction are carried out on an o-nitroaniline compound and an o-diol compound under the action of a water-soluble alkali to prepare the quinoxaline heterocyclic derivative in one step. Expensive transition metal catalysts and ligands do not need to beused, the water-soluble alkali is used as an accelerant and can be removed in a water washing manner, so that the product has no transition metal residue, the product is easy to separate, the recovery rate is high, and the method is simple in condition, easy to operate and low in equipment requirement; and the water-soluble alkali is used as the accelerant, so the unique byproduct is water, the atom economy is high, and the method has good research and industrial application prospects.

Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines

We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.