Efficient, Ecofriendly, and Practical Process for the Synthesis of Quinoxalines Catalyzed by Amberlyst-15 in Aqueous Media

Liu, Juyan; Liu, Jing; Wang, Jia-Di; Jiao, Dequan; Liu, Haiwang

doi:10.1080/00397910903219401

Cited by 34 publications

(4 citation statements)

References 27 publications

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“…Although there are several methods that afford good yields of quinoxaline, some of them suffer from drawbacks such as volatile organic solvents, unsatisfactory product yields, critical product isolation procedures, expensive and detrimental metal precursors, and harsh reaction conditions, which limit their use under the aspect of environmentally benign processes [29][30][31][32][33][34][35][36]. Initially, o-phenylenediamine and benzil was reacted at room temperature using DABCO acetic acid salt, but this was found to be time consuming and sluggish ( Table 3, entry 1).…”

Section: Resultsmentioning

confidence: 99%

Protic ionic liquids: a lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans

Mulik¹,

Chandam

Patil

et al. 2015

Res Chem Intermed

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Protic ionic liquids (PILs), which are easily produced through the combination of a Brønsted acid and Brønsted base, such as [Mim]Ac and 1,4-diazabicyclo[2.2.2]octane (DABCO):AcOH:H 2 O (1:1:3), were found to be lucid, tunable tool for synthesis of various heterocyclic motifs such as phthalazinediones, quinoxalines and benzopyrans. These PILs were found to be efficient for synthesis of diverse heterocyclic derivatives, along with demonstrating noteworthy aspects such as high yields, isolation of pure products without column chromatography and recyclable reaction media.Electronic supplementary material The online version of this article (

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Section: Resultsmentioning

confidence: 99%

Protic ionic liquids: a lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans

Mulik¹,

Chandam

Patil

et al. 2015

Res Chem Intermed

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“…The literature survey reveals several reports on the synthesis of quinoxalines using different catalysts such as p-TSA 13 oxalic acid 17 , silica bonded S-sulfonic acid 18 , ZnI 2, 19 and amberlyte-15 20 .…”

Section: Figure 1 Representative Quinoxaline Containing Drugsmentioning

confidence: 99%

An Efficient Synthesis of Quinaxoline Derivatives Using Fe(DS)3 as a Lewis Acid-Surfactant-Combined Catalyst

2016

Chem Sci Trans

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A new and eco-friendly synthetic strategy for the synthesis of quinoxaline derivatives from various 1,2-diketones and 1,2-diamines using Lewis acid-surfactant-combined Fe(DS) 3 as a water stable catalyst is described. Use of water as reaction medium rendered this procedure cost-effective and environmentally benign. In addition to its efficiency and simplicity, this method provided high yields of biologically potent quinoxalines in shorter reaction time. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.

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“…These include montmorillonite K-10, [17] o-iodoxybenzoic acid, [18] Itaconic acid, [19] polyaniline sulfate, [20] PTSA (p -Toluenesulfonic acid), [21] molecular iodine, [22,23] aqueous HF, [24] sulfamic acid, [25,26] acetic acid, [27,28] NH 4 Cl-CH 3 OH, [29] Amberlyst-15, [30] and metal catalysts such as silica-supported antimony(III) chloride, [31] cerium(IV) ammonium nitrate (CAN), [32] ZnO, [33] gallium(III) triflate, [34] zirconium(IV) chloride, [35] FeCl 3 , [36] sulfated polyborate [37] and SnCl 2 /SiO 2 . [38] A few methods for the synthesis of quinoxalines have also been reported by ultrasound irradiation [39,40] and microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

Thiourea Dioxide Catalyzed Sustainable Synthesis of Diverse Quinoxaline and Pyrazine Derivatives in Aqueous Medium at Ambient Temperature

Saini,

Manju,

Raigar

et al. 2024

ChemistrySelect

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An eco‐conscious, metal‐free protocol has been developed to synthesize a diverse collection of biologically and pharmacologically active quinoxaline and pyrazine derivatives. The protocol involves a one‐pot condensation of various 1,2‐diamines with 1,2‐diones using thiourea dioxide as a catalyst and water as a solvent at ambient temperature. Notably, the catalyst can be reused up to five times without any significant loss of efficacy. The green aspects of this method involved milder reaction conditions, higher yields with shorter reaction times, simple work‐up, non‐chromatographic separations, good reusability, and easy catalyst recovery by simple filtration. Moreover, the reaction is successfully accelerated to a multigram scale, making it favourable for production at a larger scale.

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Efficient, Ecofriendly, and Practical Process for the Synthesis of Quinoxalines Catalyzed by Amberlyst-15 in Aqueous Media

Cited by 34 publications

References 27 publications

Protic ionic liquids: a lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans

Protic ionic liquids: a lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans

An Efficient Synthesis of Quinaxoline Derivatives Using Fe(DS)3 as a Lewis Acid-Surfactant-Combined Catalyst

Thiourea Dioxide Catalyzed Sustainable Synthesis of Diverse Quinoxaline and Pyrazine Derivatives in Aqueous Medium at Ambient Temperature

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