Issue 13, 2023

Nitrogenated aromatics from chitin

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.

Graphical abstract: Nitrogenated aromatics from chitin

Supplementary files

Article information

Article type
Paper
Submitted
24 jan 2023
Accepted
13 apr 2023
First published
14 apr 2023

Green Chem., 2023,25, 5059-5067

Nitrogenated aromatics from chitin

C. S. Santos, R. Rodini Mattioli, J. Soares Baptista, V. H. Menezes da Silva, D. L. Browne and J. C. Pastre, Green Chem., 2023, 25, 5059 DOI: 10.1039/D3GC00272A

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