%X 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.
%A Renan Rodini Mattioli
%A Camila Souza Santos
%A Bruna Butke de Souza
%A Pedro Dominguez Branco
%A Robert RA Bolt
%A Sarah E Raby-Buck
%A Tadeu Luiz Gomes Cabral
%A Claudio F Tormena
%A Duncan L Browne
%A Julio C Pastre
%T On the Valorisation of Chitin-Derived Furans by Milling
%O © 2024 The Authors. ChemSusChem published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).
%D 2025
%C Germany
%L discovery10204780
%K Diels-Alder, Hydrazone, Aromatics, Chitin, Mechanochemistry
%V 18
%N 3
%J ChemSusChem
%I WILEY-V C H VERLAG GMBH