Mattioli, Renan Rodini;
Santos, Camila Souza;
de Souza, Bruna Butke;
Branco, Pedro Dominguez;
Bolt, Robert RA;
Raby-Buck, Sarah E;
Cabral, Tadeu Luiz Gomes;
... Pastre, Julio C; + view all
(2025)
On the Valorisation of Chitin-Derived Furans by Milling.
ChemSusChem
, 18
(3)
, Article e202401584. 10.1002/cssc.202401584.
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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.
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