Direct conversion of chitin derived N-acetyl-D-glucosamine into 3-acetamido-5-acetylfuran in deep eutectic solvents

3-Acetylamino-5-acetylfuran (3A5AF) is an important nitrogen-containing fine chemical with broad application prospects and high research value. Herein, we report a novel method for the conversion of N-acetyl-d-glucosamine (NAG) to 3A5AF in the choline chloride-based deep eutectic solvents (DESs). Th...

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Veröffentlicht in:Carbohydrate research 2023-02, Vol.524, p.108742-108742, Article 108742
Hauptverfasser: Wang, Kai, Xiao, Yunfei, Wu, Changchun, Feng, Yimo, Liu, Zhipeng, Zhu, Xi, Zang, Hongjun
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Sprache:eng
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Zusammenfassung:3-Acetylamino-5-acetylfuran (3A5AF) is an important nitrogen-containing fine chemical with broad application prospects and high research value. Herein, we report a novel method for the conversion of N-acetyl-d-glucosamine (NAG) to 3A5AF in the choline chloride-based deep eutectic solvents (DESs). The catalytic activities of various DESs have been smoothly screened, and DES 2 (choline chloride/PEG-200/boronic acid = 1/1/0.5) displayed the best catalytic performance. In the absence of any additional solvent, catalyst and additive, product 3A5AF was obtained in 18.3% yield after reacting at 180 °C for 15 min under atmospheric condition. In addition, DES 2 showed a good reusability. The possible reaction pathway was elucidated on the basis of the results of LC-MS and 13C NMR spectra. This study provided a new perspective for the application of DES in the conversion of chitin biomass. [Display omitted] •Direct conversion of NAG to 3A5AF in DESs without any additional solvent, catalyst and additive was realized.•3A5AF was obtained in 18.3% yield at 180 °C in a period of 15 min under normal atmospheric conditions.•The possible reaction pathways were proposed.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2023.108742