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通过研磨实现甲壳素衍生呋喃的增值利用

On the Valorisation of Chitin-Derived Furans by Milling.

作者信息

Mattioli Renan Rodini, Santos Camila Souza, de Souza Bruna Butke, Branco Pedro Dominguez, Bolt Robert R A, Raby-Buck Sarah E, Gomes Cabral Tadeu Luiz, Tormena Claudio F, Browne Duncan L, Pastre Julio C

机构信息

Institute of Chemistry, State University of Campinas (UNICAMP), Campinas, SP, 13083-970, Brazil.

Department of Pharmaceutical and Biological Chemistry, School of Pharmacy, University College London (UCL), 29-39 Brunswick Square, London, WC1N 1AX, UK.

出版信息

ChemSusChem. 2025 Feb 1;18(3):e202401584. doi: 10.1002/cssc.202401584. Epub 2024 Oct 30.

DOI:10.1002/cssc.202401584
PMID:39240242
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11790004/
Abstract

Chitin-derived furans offer a sustainable alternative feedstock for nitrogen appended aromatic compounds. Herein, we address the challenge of using chitin-derived furans, 3-acetamido-5-acetylfuran (3A5AF) and 3-acetamido-5-furfural aldehyde (3A5F), to favour the formation of exo Diels-Alder adducts and 4-acetylaminophthalimides respectively, using a mechanochemical ball-milling technique. Mechanochemical activation is explored through the synthesis of 7-oxa-norbornene backbones with novel substitution pattern from 3A5AF in yields up to 77 % and improved exo:endo selectivity compared to solution-phase reactions. The synthesis of 4-acetylaminophthalimides from 3A5F in yields up to 79 % is also showcased from hydrazone derivatives.

摘要

几丁质衍生的呋喃为含氮芳香族化合物提供了一种可持续的替代原料。在此，我们应对了使用几丁质衍生的呋喃（3-乙酰氨基-5-乙酰基呋喃（3A5AF）和3-乙酰氨基-5-糠醛（3A5F））分别促进外型狄尔斯-阿尔德加合物和4-乙酰氨基邻苯二甲酰亚胺形成的挑战，采用了机械化学球磨技术。通过从3A5AF合成具有新型取代模式的7-氧杂降冰片烯主链来探索机械化学活化，产率高达77%，与溶液相反应相比，外型：内型选择性得到了改善。还展示了由腙衍生物从3A5F合成产率高达79%的4-乙酰氨基邻苯二甲酰亚胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/a3dafb1e8e8d/CSSC-18-e202401584-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/5b18812846ab/CSSC-18-e202401584-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/fffca395622f/CSSC-18-e202401584-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/f5d4cc46b96c/CSSC-18-e202401584-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/8a66b21a784a/CSSC-18-e202401584-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/49e20ad00209/CSSC-18-e202401584-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/a3dafb1e8e8d/CSSC-18-e202401584-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/5b18812846ab/CSSC-18-e202401584-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/fffca395622f/CSSC-18-e202401584-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/f5d4cc46b96c/CSSC-18-e202401584-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/8a66b21a784a/CSSC-18-e202401584-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/49e20ad00209/CSSC-18-e202401584-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b21/11790004/a3dafb1e8e8d/CSSC-18-e202401584-g010.jpg

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本文引用的文献

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Green metrics in mechanochemistry.机械化学中的绿色指标
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