Formation of a Renewable Amine and an Alcohol via Transformations of 3-Acetamido-5-acetylfuran

Liu, Yi; Stähler, Cosima; Murphy, Jennifer N.; Furlong, Brandon J.; Kerton, Francesca M.

doi:10.1021/acssuschemeng.7b00323

Cited by 43 publications

(34 citation statements)

References 36 publications

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“…3A5AF has the potential to become an important building block for N‐containing aromatic chemicals, and examples of its utilization are present in the literature . This compound was first obtained as a byproduct in a low yield in the pyrolysis of chitin .…”

Section: Methodsmentioning

confidence: 99%

“…3A5AF has the potentialt ob ecome an important building block for N-containinga romatic chemicals, and examples of its utilization are present in the literature. [9][10][11][12][13] This compound was first obtained as ab yproduct in al ow yield in the pyrolysis of chitin. [14][15][16] Recently,l iquid-phase reactions to synthesize 3A5AFf rom NAG have been proposed.H owever,t he production of 3A5AF has been proven to be ac hallengingr eaction, and often non-conventional methods or harsh conditions are employed.…”

mentioning

confidence: 99%

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Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts

2020

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3‐Acetamido‐5‐acetylfuran (3A5AF) is a promising intermediate obtained from chitin for the production of N‐containing value‐added chemicals. However, the synthetic method is complicated so far, which has limited further investigation using 3A5AF. Herein, a facile method was developed for synthesizing 3A5AF from N‐acetyl‐d‐glucosamine (NAG), including a simple isolation procedure. A 30 % yield of 3A5AF was obtained by performing the dehydration of NAG in N,N‐dimethylformamide (DMF) solvent in the presence of AlCl3⋅6 H2O at a temperature as low as 120 °C by conventional heating for 30 min. This method tolerated a wide range of temperature and concentration of substrate, thus easily allowing scale‐up of the reaction. The produced 3A5AF was isolated with 98 % purity by simple column chromatography. Additionally, a highly functionalized N‐containing lactone was identified as a byproduct under these reaction conditions.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts

2020

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“…Unfortunately, the chemical structures of products have not been identified, and the yields of products have not been reported. The same group [43] demonstrated the hydrolysis of 3A5AF over NaOH, affording 2acetyl-4-aminofuran in 57 % yield at 80°C for 1 h. Meanwhile, the reduction of 3A5AF by isopropyl alcohol over IrH 2 Cl [( i Pr 2 PC 2 H 4 ) 2 NH] in the presence of potassium tert-butoxide was performed, and a secondary alcohol, 3-acetamido-5-(1-hydroxylethyl)furan was obtained at room temperature for 2.5 h in 80 % isolated yield. [43] Similar to previous findings, [42] the dehydration of 3-acetamido-5-(1-hydroxylethyl)furan was apt to occur, giving corresponding alkene.…”

Section: Conversion Of Nag-derived 3a5af To Heterocyclic Compoundsmentioning

confidence: 99%

Towards Shell Biorefinery: Advances in Chemical‐Catalytic Conversion of Chitin Biomass to Organonitrogen Chemicals

Dai

2020

ChemSusChem

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Chitin is the most abundant biopolymer after cellulose but it has not been fully utilized yet. Because of biologically fixed nitrogen, effective conversion of chitin or its derivatives to value‐added organonitrogen compounds is a promising strategy to valorize chitin biomass, which has attracted increasing attention. Recently, a novel concept of shell biorefinery has been proposed on account of the huge potentials of chitin valorization. Until now, a number of valuable organonitrogen chemicals, including amino sugars, amino alcohols, amino acids, and heterocyclic compounds, have been produced from chitin biomass. In this Minireview, the focus is on the recent advances in the synthesis of organonitrogen chemicals employing chitin biomass as starting material via different catalytic processes. An outlook on the challenges and opportunities for more effective valorization of chitin will be given.

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“…Under certain conditions, the spontaneous formation of alkene 3 was observed probably due to the elimination of the formed alcohol. Upon the use of a stronger reductant such as lithium aluminum hydride, both carbonyls were reduced and the cyclic structure of the furan ring was opened . The reaction of 3A5AF with several ketones such as acetone, butanone or benzophenone surprisingly yielded a novel dihydrofuropyridine scaffold 6 , and produced 4 with formaldyhyde via hydroxymethylation of the furan ring.…”

Section: O-containing Chemicalsmentioning

confidence: 99%

Sustainable Routes for the Synthesis of Renewable Heteroatom-Containing Chemicals

Hülsey

Yang

Yan

2018

ACS Sustainable Chem. Eng.

153

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One of the biggest discrepancies between the structure of many utilized chemicals and petrochemicals is the ubiquity of heteroatoms in the former and the lack thereof in the latter. Many commodity chemicals and almost all specialty chemicals and pharmaceuticals contain one or more heteroatoms, but introducing functionalities containing oxygen, nitrogen, sulfur or phosphorus into crude oil-derived chemicals is often a very energy- and resource-intensive endeavor. This and the inevitable depletion of fossil resources in the not too distant future are the main reasons for the development of sustainable ways to produce compounds bearing heteroatoms. Synthesis of oxygen-containing compounds from renewable resources such as starch, cellulose and hemicellulose is already well-known, and the production of phenolic compounds from lignin is garnering significant attention recently. In the meantime, there is a surge in the valorization of chitin from waste crustacean and insect shells for the production of various nitrogen-containing compounds. Much less explored is the valorization of sulfur- and phosphorus-containing biomass components, although they find some high market value applications. Catalysis plays a central role to enable the conversion of biomass into value-added products with high activity and selectivity. Further developments made by chemical engineers and process technologists will be required to make those processes economically feasible and competitive with current synthetic schemes from fossil resources. This perspective highlights the most recent advances and the upcoming challenges in the development of renewable and sustainable routes toward heteroatom-containing chemicals.

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Formation of a Renewable Amine and an Alcohol via Transformations of 3-Acetamido-5-acetylfuran

Cited by 43 publications

References 36 publications

Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts

Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts

Towards Shell Biorefinery: Advances in Chemical‐Catalytic Conversion of Chitin Biomass to Organonitrogen Chemicals

Sustainable Routes for the Synthesis of Renewable Heteroatom-Containing Chemicals

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