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.
Authors
- Xinyue Fang
- Dongni Hu
- Zhihui Guo (ORCID: https://orcid.org/0000-0002-4629-0184)
- Yanfei Zhao (ORCID: https://orcid.org/0000-0003-3369-1779)
- Ling Wu (ORCID: https://orcid.org/0000-0003-2652-8105)
- Xingying Lan (ORCID: https://orcid.org/0000-0002-9034-2711)
- Fengtian Wu (ORCID: https://orcid.org/0000-0002-0760-809X)
- Zhimin Liu (ORCID: https://orcid.org/0000-0001-7953-7414)
- Tao Xie (ORCID: https://orcid.org/0000-0001-9364-5083)
- Yuepeng Wang (ORCID: https://orcid.org/0000-0002-7938-5948)
- Dongyan Liu
Institutions
- Chinese Academy of Sciences (CN)
- China University of Petroleum, Beijing (CN)
- Beijing National Laboratory for Molecular Sciences (CN)
- East China University of Technology (CN)
- Institute of Chemistry (CN)
Publication Details
- Journal
- Industrial & Engineering Chemistry Research
- Published
- 2024-11-22
- DOI
- https://doi.org/10.1021/acs.iecr.4c03197
- Primary Topic
- Chemical Synthesis and Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Key Research and Development Program of China