The use of non-conventional solvent systems, such as deep eutectic solvents (DES), for biomass processing is a growing interest. DES are formed by two or more components, usually solids at room temperature, which can interact with each other via hydrogen bonding, from a hydrogen bond acceptor (HBA) and a hydrogen bond donor (HBD), resulting in a liquid phase. The most studied HBA in the literature is choline chloride with several HBD and their use have been extensively reviewed. However, other abundant and natural HBA can be successfully applied on the preparation of different DES, e.g., amino acids. These amino acid-based DES have been used in biomass pretreatment, providing the fractionation of the main macromolecular components by lignin solubilization. In addition, amino acid-based DES can be applied in biomass chemical conversion to obtaining platform chemicals such as furanic derivatives. Bearing this in mind, this review focuses on exploring the use of amino acid-based DES on biomass processing, from pretreatment to chemical conversion.
The application of biomass-derived furans in sequential Diels-Alder (DA)/aromatization reactions is a promising approach for the preparation of aromatic compounds with different substitution patterns. In this work, we addressed the challenge of using chitin-derived furans, 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 DA adduct, 7-oxa-norbornene, which in an acid/acetylating medium undergoes a dehydration/aromatization reaction, providing the compounds in yields ranging from 16-80%. To the best of our knowledge, this is the first report involving a chitin derivative for the formation of 4-Acetylaminophthalimides, which is the first step towards expanding the toolbox of chitin-derived furans in the synthesis of nitrogenated aromatic compounds with the nitrogen atom directly attached to the benzene ring.
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 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%. To the best of our knowledge, we describe the first report involving a chitin derivative for the formation of 4-acetylaminophthalimides, which 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.
In this work, we addressed the challenge of using chitin-derived furans, 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 DA adduct, 7-oxa-norbornene, which in an acidic/acetylating medium undergoes a dehydration/aromatization process providing nitrogenated aromatic compounds in yields ranging from 16–80%. To the best of our knowledge, this is the first report involving a chitin derivative for the formation of 4-acetylaminophthalimides, which is the first step towards expanding the toolbox of chitin-derived furans in the synthesis of nitrogenated aromatic compounds with the nitrogen atom directly attached to the benzene ring.
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