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An expeditious and greener synthesis of 2-aminoimidazoles in deep eutectic solvents

机译:在低共熔溶剂中快速,绿色合成2-氨基咪唑

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摘要

A high-yield one-pot two-step synthesis of 2-aminoimidazoles (2-AI), exploiting an under-air heterocyclodehydration process between α-chloroketones and guanidine derivatives, and using deep eutectic solvents (DESs) as nonconventional, "green" and "innocent" reaction media, has been accomplished successfully. The combination of either glycerol or urea with choline chloride (ChCl) proved to be effective for decreasing the reaction time to about 4-6 h in contrast to the 10-12 h usually required for the same reaction run in toxic and volatile organic solvents and under an argon atmosphere. In addition, the use of the ChCl-urea as a DES also enables the direct isolation of triaryl-substituted 2-AI derivatives by means of a simple work-up procedure consisting in filtration and crystallization, and allows the recycle of the DES mixture. A plausible mechanism highlighting the potential role played by hydrogen bonding catalysis has also been illustrated.
机译:高产一锅二步合成2-氨基咪唑(2-AI),利用空气中α-氯酮和胍衍生物之间的杂环脱水过程,并使用深共熔溶剂(DESs)作为非常规的“绿色”和“无辜的”反应介质已经成功完成。事实证明,甘油或尿素与氯化胆碱(ChCl)的组合可有效减少反应时间至约4-6 h,而在有毒和挥发性有机溶剂中进行相同反应通常需要10-12 h。在氩气气氛下。另外,使用ChCl-脲作为DES还可以通过包括过滤和结晶的简单后处理程序直接分离三芳基取代的2-AI衍生物,并允许DES混合物的再循环。还阐明了一个合理的机制,强调了氢键催化作用的潜在作用。

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