IC2MP UMR CNRS, Université de Poitiers 7285, ENSIP 1 rue Marcel Doré, TSA 41195, 86073, Poitiers Cedex 9, France.
Published: April 2020
AI Article Synopsis
Article Abstract
The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan-derived amines was developed [e.g., 1-(furan-2-yl)-4-methylpentan-2-amine] with high yield (up to 95 %) from (E)-1-(furan-2-yl)-5-methylhex-1-en-3-one. The catalyst used was Ru/C, and it was recyclable up to the fourth cycle. To further realize cost-efficiency, a one-reactor tandem concept was attempted. To this aim direct reaction from furfural was investigated. A high yield (74 %) towards 1-(furan-2-yl)-4-methylpentan-2-amine could be achieved starting directly from furfural in the presence of methyl isobutyl ketone, NH , H , and Ru/C catalyst.
Furan-based amines are highly valuable compounds which can be directly obtained via reductive amination from easily accessible furfural, 5-(hydroxymethyl)furfural (HMF) and 2,5-diformylfuran (DFF). Herein the biocatalytic amination of these carbonyl derivatives is disclosed using amine transaminases (ATAs) and isopropylamine (IPA) as amine donors. Among the different biocatalysts tested, the ones from Chromobacterium violaceum (Cv-TA), Arthrobacter citreus (ArS-TA), and variants from Arthrobacter sp.
The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan-derived amines was developed [e.g.
A short and concise sequence for the synthesis of symmetrically and unsymmetrically substituted 3,3'-linked bispyrroles is described. Furan as a starting material is subjected to a twofold cyclopropanation by a diazo ester. Conversion of the ester functionalities to the respective ketones is achieved via Weinreb amide formation and the attack of a Grignard reagent.
In vitro incubation of rat liver microsomes with [14C]-furan in the presence of NADPH resulted in the covalent incorporation of furan-derived radioactivity in microsomal protein. Compared to microsomes from untreated rats a two- to threefold increase in binding was observed with microsomes from phenobarbital-treated rats and a four- to five-fold increase was observed with microsomes from rats pretreated with imidazole or pyrazole. Covalent binding was reduced with microsomes from rats pretreated with beta-naphthoflavone.
