Nitrogenated aromatics from chitin

Author(s)

Santos, Camila Souza ; Mattioli, Renan Rodini ; Baptista, Julia Soares ; da Silva, Vitor Menezes H. ; Browne, Duncan L. ; Pastre, Julio Cezar

• Document type: Journal article
• Source: GREEN CHEMISTRY; v. 25, n. 13, p. 10-pg., 2023-04-14.

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. (AU)

• FAPESP's process: 19/26450-9 - Application of green chemistry in Synhtesis of materials and building blocks employing renewable resources and continuous flow syntesis
• Grantee: Renan Rodini Mattioli
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 22/03872-8 - Mechanochemical synthesis of nitrogen-functionalized compounds obtained from biomass derivatives
• Grantee: Renan Rodini Mattioli
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 21/06661-5 - Enabling technologies for the sustainable chemical synthesis of platform molecules, new chemicals and bioactive compounds
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Young Investigators Grants - Phase 2
• FAPESP's process: 22/00774-5 - Employment of renewable chemical platforms to obtain synthetic intermediates with higher added-value.
• Grantee: Camila Souza Santos
• Support Opportunities: Scholarships in Brazil - Post-Doctoral