Dicationic Ionic Liquid Mediated Synthesis of 5‐Arylidine‐2,4‐thiazolidinediones

Abstract

An efficient synthesis of 5-arylidine-2,4-thiazolidinediones has been developed using dicationic ionic liquid as green medium and catalyst. This method performed well for the condensation of both aryl as well as heteryl aldehydes with 2,4-thiazolidinedione and gave 5-arylidine-2,4-thiazolidinediones with excellent yields.

Polyethylene Glycol: A New Medium for Green Organic Synthesis

“…7.1 形成五元杂环 噻唑是一类重要的五元杂环. 在室温和无催化剂条 件下, PEG-400 对甲基芳酮 [68] 、α-卤代酮 [69] 以及甲苯磺 酸根甲基酮 [70] 和硫酰胺或取代硫脲反应生成多取代噻 唑, 具有较好的促进作用(Scheme 7). 这类反应对底物 所含官能团适应性宽, 产率在 85%以上.…”

A convenient approach to synthesize substituted 5-Arylidene-3-m-tolyl thiazolidine-2, 4-diones by using morpholine as a catalyst and its theoretical study

“…Several methods have been reported up to date for the synthesis of thiazolidine-2,4-dione and its derivatives with an extensive range of catalysts including Alum [22], glycine, sodium carbonate, piperidinium acetate [23], piperidine [24], amines salts [25], baker's yeast [26], ionic liquids [27][28][29][30][31] and nanoparticle-supported copper (II) catalysts [32]. However, several of these existing methods suffer from one or more drawbacks, such as low yields, long reaction times, environmentally unfavorable solvents, and a requirement for excess catalyst.…”

A Solvent-Free Protocol for the Green Synthesis of 5-Arylidene-2,4-thiazolidinediones Using Ethylenediamine Diacetate as Catalyst

“…, baker's yeast [18], KF-Al 2 O 3 under microwave irradiation [19], glycine under microwave irradiation [20], and polyethylene glycol-300 at 100-120 • C [21]. Recently, ionic liquids ([bnmim]Cl, C 3 [min] 2 ·2[Br − ]) catalyzed synthesis of 5-arylidene-2,4thiazolidinediones have also been reported [22,23]. Each of these methods have their own advantages but also suffer from one or more disadvantages such as long reaction times, low to moderate yields, tedious work-up procedures, requirement of special apparatus, use of organic solvents, requirement of excess of catalysts, and difficulty in recovery and reusability of the catalysts.…”