在离子液体 1-羟乙基-3-甲基咪唑鎓乙酸酯上氢键催化合成噁唑烷酮

IF 3.8 3区工程技术 Q2 ENGINEERING, CHEMICAL Industrial & Engineering Chemistry Research Pub Date : 2024-11-22 DOI:10.1021/acs.iecr.4c03197

Fengtian Wu, Zewei Guo, Xinyue Fang, Xingying Lan, Yanfei Zhao, Yuepeng Wang, Dongyan Liu, Tao Xie, Delin Hu, Ling Wu, Zhimin Liu

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引用次数: 0

摘要

在此，我们报告了在离子液体 1-hydroxyethyl-3-methylimidazolium acetate ([OH-EMIm][OAc])上以氢键催化 1,2-苄胺、氧化苯乙烯和碳酸二甲酯的三组分反应，在 100 °C 下以极好的收率合成各种噁唑烷酮。这表明[OH-EMIm][OAc]能通过氢键活化 1,2-苄胺和氧化苯乙烯，形成中间体 2-（苄基氨基）-1-苯基-1-醇，该中间体进一步与[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作用生成噁唑烷酮。此外，[OH-EMIm][OAc]可重复使用五次而不会失去活性。该方案提供了一种简便而新颖的草唑烷酮路线，具有广阔的应用前景。

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Hydrogen Bond-Catalyzed Synthesis of Oxazolidinone over Ionic Liquid 1-Hydroxyethyl-3-methylimidazolium Acetate

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.

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来源期刊

Industrial & Engineering Chemistry Research 工程技术-工程：化工

CiteScore

7.40

自引率

7.10%

发文量

1467

审稿时长

2.8 months

期刊介绍： ndustrial & Engineering Chemistry, with variations in title and format, has been published since 1909 by the American Chemical Society. Industrial & Engineering Chemistry Research is a weekly publication that reports industrial and academic research in the broad fields of applied chemistry and chemical engineering with special focus on fundamentals, processes, and products.