Herein, we report a hydrogen bonding-catalyzed three-component reaction of 1,2-benzylamine, styrene oxide, and dimethyl carbonate over ionic liquid 1-hydroxyethyl-3-methylimidazolium acetate ([OH-EMIm][OAc]) to synthesize various oxazolidinones in excellent yields at 100 °C. This indicates that [OH-EMIm][OAc] can activate 1,2-benzylamine and styrene oxide through hydrogen bonding to form intermediate 2-(benzylamino)-1-phenylethan-1-ol, which further reacts with dimethyl carbonate activated by [OH-EMIm][OAc], producing oxazolidinone via intramolecular cyclization of the intermediate methyl benzyl(hydroxy(phenyl)methyl)carbamate. Moreover, [OH-EMIm][OAc] could be reused five times without loss of activity. This protocol provides a facile and novel route to oxazolidinones, which may have promising application potential.

中文翻译：

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氢键催化的氧唑烷酮在离子液体 1-羟乙基-3-甲基咪唑乙酸鎓上的合成


在此，我们报道了 1,2-苄胺、苯乙烯氧化物和碳酸二甲酯在离子液体 1-羟乙基-3-甲基咪唑乙酸铵 （[OH-EMIm][OAc]） 上的氢键催化三组分反应，在 100 °C 下以优异的产率合成了各种恶唑烷酮。 这表明[OH-EMIm][OAc]可以通过氢键活化1,2-苄胺和苯乙烯氧化物，形成中间体2-（苄基氨基）-1-苯乙烷-1-醇，后者进一步与[OH-EMIm][OAc]活化的碳酸二甲酯反应，通过中间体甲基苄基（羟基（苯基）甲基）氨基甲酸酯的分子内环化生成恶唑烷酮。此外，[OH-EMIm][OAc] 可以重复使用 5 次而不会失去活性。该方案提供了一种简单而新颖的噁唑烷酮类药物途径，可能具有有前途的应用潜力。