On the Valorisation of Chitin‐Derived Furans by Milling
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.
Authors
- T. Cabral (ORCID: https://orcid.org/0000-0003-3222-065X)
- Robert R. A. Bolt (ORCID: https://orcid.org/0000-0002-9721-4931)
- Cláudio F. Tormena (ORCID: https://orcid.org/0000-0002-1508-0694)
- Duncan L. Browne (ORCID: https://orcid.org/0000-0002-8604-229X)
- Pedro Dominguez Branco (ORCID: https://orcid.org/0000-0001-5655-2590)
- Renan Rodini Mattioli (ORCID: https://orcid.org/0000-0001-5952-1941)
- Sarah E. Raby‐Buck (ORCID: https://orcid.org/0000-0003-2561-3885)
- Julio Cezar Pastre (ORCID: https://orcid.org/0000-0001-9972-425X)
- Camila Souza Santos (ORCID: https://orcid.org/0000-0003-0540-9342)
- Bruna Butke de Souza
Institutions
- Universidade Estadual de Campinas (UNICAMP) (BR)
- University College London (GB)
Publication Details
- Journal
- ChemSusChem
- Published
- 2024-09-06
- DOI
- https://doi.org/10.1002/cssc.202401584
- Citations
- 5
- Primary Topic
- Chemical synthesis and alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico