Santos, Camila Souza;
Rodini Mattioli, Renan;
Soares Baptista, Julia;
Menezes da Silva, Vitor H;
Browne, Duncan L;
Pastre, Julio Cezar;
(2023)
Nitrogenated aromatics from chitin.
Green Chemistry
, 25
(13)
pp. 5059-5067.
10.1039/d3gc00272a.
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Abstract
Herein, we addressed the challenge of using two chitin-derived furans, namely 3-acetamido-5-ethylfuran (3A5EF) and 3-acetamido-5-(1-hydroxyethyl)furan (3A5HF), for the formation of 4-acetylaminophthalimides and other N-containing aromatic compounds. The transformation is carried out sequentially and involves the formation of the Diels–Alder adduct, forming a 7-oxa-norbornene backbone, which, in an acidic/acetylating medium, undergoes a dehydration/aromatisation process providing nitrogenated aromatic compounds in yields ranging from 16–80%. The preparation of 4-acetylaminophthalimides from a chitin derivative is the first step towards expanding the toolbox of chitin-derived furans in the synthesis of unique nitrogenated aromatic compounds with the nitrogen atom directly attached to the benzene ring.
| Type: | Article |
|---|---|
| Title: | Nitrogenated aromatics from chitin |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/d3gc00272a |
| Publisher version: | https://doi.org/10.1039/D3GC00272A |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10171670 |
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