Nitrogenated aromatics from chitin

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 sequentiall...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-07, Vol.25 (13), p.559-567
Main Authors: Santos, Camila Souza, Rodini Mattioli, Renan, Soares Baptista, Julia, Menezes da Silva, Vitor H, Browne, Duncan L, Pastre, Julio Cezar
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzene
Chitin
Dehydration
Furans
Green chemistry
Pesticides
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Summary: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. DA adducts obtained from chitin-derived furans underwent dehydration reactions ultimately leading to the synthesis of N -containing aromatics, including phthalimides.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc00272a