An efficient synthesis of quinoxaline derivatives mediated by stannous chloride
TL;DR: In this paper, the role of stannous chloride is acting as both reductive agent and catalyst in the synthesis of quinoxaline derivatives, which has the advantages of accessible starting materials, convenient manipulation, short reaction time and high yields.
About: This article is published in Journal of Heterocyclic Chemistry.The article was published on 2008-11-01. It has received 35 citations till now. The article focuses on the topics: Quinoxaline & Chloride.
Citations
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TL;DR: In this review the State of the Art will be presented, which includes a summary of the progress made over the past years in the knowledge of the structure and mechanism of the quinoxaline and quInoxaline derivatives, associated medical and biomedical value as well as industrial value.
281 citations
TL;DR: This review focusses on the quinoxaline derivatives developed during the last decennial period and their biomedical applications.
113 citations
TL;DR: In this paper, an environmentally friendly procedure for the synthesis of quinoxaline derivatives in the presence of magnetic Fe3O4 nanoparticles was developed for water-powered synthesis of 1,2-diamines and 1, 2-dicarbonyl compounds.
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.
79 citations
TL;DR: An efficient and inexpensive sulfated polyborate catalyst was applied for the rapid synthesis of quinoxaline derivatives from various substituted o-phenylenediamines and 1,2-diketones/α-hydroxy ketones.
Abstract: An efficient and inexpensive sulfated polyborate catalyst was applied for the rapid synthesis of quinoxaline derivatives from various substituted o-phenylenediamines and 1,2-diketones/α-hydroxy ketones using sulfated polyborate is described. The catalyst has the advantage of Lewis as well as Bronsted acidity and recyclability without significant loss in catalytic activity. The key advantages of the present method are high yields, short reaction times, solvent-free condition, easy workup, and ability to tolerate a variety of functional groups, which give economical as well as ecological rewards.
55 citations
TL;DR: In this article, the scope and limitations of surfactants as catalysts for the synthesis of quoxalines using microreactors made of the surfactant in water has been assessed.
Abstract: The scope and limitations of surfactants as catalysts for the synthesis of quinoxalines using microreactors made of the surfactants in water has been assessed The catalytic potential followed the order: non-ionic surfactants > anionic surfactants > Bronsted acid surfactants > cationic surfactants The non-ionic surfactant, Tween 40, is the most effective catalyst affording excellent yields within a short reaction time at room temperature and is compatible with different variations of the 1,2-diketones and 1,2-diamines The reaction medium (spent water) containing the catalyst, as well as the catalyst itself (recovered Tween 40) can be reused for five consecutive reactions The better catalytic efficiency of the surfactant (Tween 40) compared to the various Lewis/Bronsted acids, as well as the surfactant combined Lewis acid, suggests that surfactants, which generate microreactor assemblies at the interface, are better suited as catalytic aids to promote organic reactions in water The inferior results obtained in organic solvents, which provide a homogeneous reaction mixture compared to those obtained in water, indicate the specific role of water This has been depicted as a synergistic dual activation through the hydrogen bond mediated formation of supramolecular assemblies involving a water dimer and the reactants The catalytic assistance of the surfactant could be ascribed to the ability of the surfactant molecule to undergo hydrophobic and hydrogen bond forming interactions with water and the reactants in orienting the reactants at the water interface and encapsulating inside the microreactors to facilitate the cyclocondensation
54 citations
References
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TL;DR: In this article, the minority charge carrying capacity of the homopolymers is probed: it is shown that the quinoxaline derivative has hole blocking properties superior to those of the oxadiazole polymer and is a good candidate for use in optimised devices.
Abstract: Improved syntheses and polymerisations are reported of monomers bearing electron transporting substituents based on 2,5-diphenyloxadiazole and 2,3-diphenylquinoxaline attached directly to a vinyl group. By copolymerisation and by use of mixtures of homopolymers, these materials have been incorporated into light emitting polymer devices in which hole conduction properties are provided by 4-vinyltriphenylamine groups. High luminescence efficiency is achieved by use of a fluorescent additive. The resulting devices show narrow emission bands and high brightnesses, except in the case of those based on a diphenyloxadiazole–triphenylamine polymer blend. Thermal analysis data are equivocal but we present evidence that in this system, but not the quinoxaline blend, phase separation occurs. The minority charge carrying capacity of the homopolymers is probed: it is shown that the quinoxaline derivative has hole blocking properties superior to those of the oxadiazole polymer and is
a good candidate for use in optimised devices.
339 citations
TL;DR: In this article, a Pd-catalyzed C−N coupling reaction was used to tune the photophysical and thermal properties of electroluminescent materials, including quinoxaline, triarylamine, and fluorophores.
Abstract: Electroluminescent materials comprising quinoxaline, triarylamine, and fluorophores such as carbazole, pyrene, and fluorene were prepared by using a key step involving a Pd-catalyzed C−N coupling reaction. Chromophores were embedded both at quinoxaline and triarylamine units, and their influence on photophysical and thermal properties was investigated. Quinoxalines possessing more electron-donating amines exhibit lower fluorescence quantum efficiency and the photoluminescence (PL) is severely affected by the polarity of the solvent used for measurement. Bulky and rigid aromatic groups such as pyrene and carbazole enhance the glass transition temperature of the derivatives. Oxidation potential of the triarylamine was easily tuned by the aromatic substituents while retaining the reduction potential of the quinoxaline segment. This provides us a method for tuning the photophysical and thermal properties maintaining the energy levels of the dipolar compounds. The electroluminescent devices fabricated using th...
266 citations
TL;DR: The compound 1a shows remarkable cytotoxicities against human tumor various cell lines, and is active VRE (vancomycin-resistant enterococci) within MIC range 0.5-8 microg/mL.
260 citations
TL;DR: The use of molecular iodine as the catalyst for a one-pot synthesis of quinoxaline derivatives at room temperature was reported in this article, where it was shown that molecular iodine can be used as a catalyst for any onepot synthesis.
249 citations
TL;DR: In this paper, the use of poly(phenyl quinoxaline) (PPQ) as an electron transporting conjugated polymer for electroluminescence (EL) applications was reported.
Abstract: We report the use of a poly(phenyl quinoxaline) (PPQ) as an electron transporting conjugated polymer for electroluminescence (EL) applications. Single‐layer PPQ devices with ITO anode and aluminium cathode show unipolar electron transport with current densities up to 60 mA/cm2 but no emission. Two‐layer structures combining PPQ as electron transport material with the hole transporting poly(2,5‐dialkoxy‐p‐phenylene vinylene) (PDAOPV) show strong emission from the PDAOPV with brightnesses up to 250 cd/m2. These two‐layer structures have a maximum EL quantum efficiency of 0.35% which is ten‐fold enhanced compared with the corresponding single‐layer PDAOPV devices.
232 citations