Magnetic Fe3O4 Nanoparticles as New, Efficient, and Reusable Catalysts for the Synthesis of Quinoxalines in Water

Abstract

A novel, environmentally friendly procedure has been developed for the synthesis of quinoxaline derivatives in the presence of magnetic Fe3O4 nanoparticles. The reaction between 1,2-diamines and 1,2-dicarbonyl compounds was carried out in water to afford quinoxaline derivatives in high yield. The catalyst can be recovered by the use of an external magnet and reused for five cycles with almost consistent activity.

Fe 3 O 4 @SiO 2 –imid–PMA n magnetic porous nanosphere as recyclable catalyst for the green synthesis of quinoxaline derivatives at room temperature and study of their antifungal activities

“…Quinoxalines are very important compounds due to their wide spectrum of biological activities behaving as anticancer [1], antiviral [2], antibacterial [3][4][5] and activity as kinase inhibitors [6]. Also, quinoxaline moieties have found applications in macro cyclic receptors [7], chemically controllable switches [8], building blocks in the synthesis of organic semiconductors [9], electroluminescent materials [10], organic semiconductors [11], dehydroannulenes [12], DNA cleaving agents [13], antiinflammatory, anti-protozoal and anti-HIV [14,15].…”

Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives

“…Heterogeneous catalysis characterizes one of the oldest commercial practices of nanoscience, nanoparticles of metals and other compounds have been extensively used for important chemical reactions. Fe 3 O 4 nanoparticles (Fe 3 O 4 NPs) have been used as recyclable catalysts in the development of sustainable methodologies [47] for synthesis of compounds such as xanthenes [48], oximes [49], quinoxalines [50], fused azo-linked pyrazolo[4,3-e]pyridines [51], 1,8-dioxo-decahydroacridine [52], propargylamines [53] and many more, because of their significant characteristics such as the ease of magnetic separation from the reaction mixture, non-toxicity, and being widely accessible. But Fe 3 O 4 NPs has never been used in the synthesis of tetrahydro-4H-chromene (4a-x) and 1,4-dihydropyridine (7a-t) derivatives.…”

An Efficient and Recyclable Nanoparticle-Supported Cobalt Catalyst for Quinoxaline Synthesis

“…Generally, quinoxalines can be prepared via a double condensation of 1,2-phenylenediamines with 1,2-diketones [24][25][26][27][28]. A number of reagents have been shown to catalyze these reactions such as acidic alumina [29], citric acid [30], magnetic Fe3O4 nanoparticles in H2O [31], silica-bonded sulfonic Generally, quinoxalines can be prepared via a double condensation of 1,2-phenylenediamines with 1,2-diketones [24][25][26][27][28]. A number of reagents have been shown to catalyze these reactions such as acidic alumina [29], citric acid [30], magnetic Fe 3 O 4 nanoparticles in H 2 O [31], silica-bonded sulfonic acid [32], among others [33,34].…”

“…A number of reagents have been shown to catalyze these reactions such as acidic alumina [29], citric acid [30], magnetic Fe3O4 nanoparticles in H2O [31], silica-bonded sulfonic Generally, quinoxalines can be prepared via a double condensation of 1,2-phenylenediamines with 1,2-diketones [24][25][26][27][28]. A number of reagents have been shown to catalyze these reactions such as acidic alumina [29], citric acid [30], magnetic Fe 3 O 4 nanoparticles in H 2 O [31], silica-bonded sulfonic acid [32], among others [33,34]. Other protocols to synthesize quinoxalines mainly involve the oxidative trapping of vicinal diols or α-hydroxy ketones with 1,2-diamines [35][36][37][38][39][40][41][42], 1,4-addition of 1,2-diamines to diazenylbutenes [43], coupling of epoxides with ene-1,2-diamines [44,45], 2-nitroanilines with phenethylamines [46], alkynes or ketones with 1,2-diamines via a key oxidation process [47][48][49][50][51].…”