1240163-58-9Relevant academic research and scientific papers
A biosynthesis-inspired approach to over twenty diverse natural product-like scaffolds
Firth, James D.,Craven, Philip G. E.,Lilburn, Matthew,Pahl, Axel,Marsden, Stephen P.,Nelson, Adam
, p. 9837 - 9840 (2016)
A synthetic approach to diverse scaffolds was developed that was inspired by diterpene biosynthesis. Initial scaffolds, generated using Diels-Alder reactions of furyl-functionalised amines, were transformed into alternative scaffolds using cleavage, ring expansion, annulation and rearrangement reactions. In total, 25 diverse scaffolds were prepared that were shown to have high natural product-likeness.
Synthesis of Bis(hydroxylmethylfurfuryl)amine Monomers from 5-Hydroxymethylfurfural
Xu, Zhanwei,Yan, Peifang,Liu, Kairui,Wan, Lu,Xu, Wenjuan,Li, Huixiang,Liu, Xiumei,Zhang, Z. Conrad
, p. 1255 - 1258 (2016)
We report the synthesis of bis(hydroxylmethylfurfuryl)amine (BHMFA) from 5-hydroxymethylfurfural (5-HMF) by reacting 5-HMF with primary amines in the presence of homogeneous RuII catalysts having sterically strained ligands. BHMFA is a group of furan-based monomers that offer great potential to form functional biopolymers with tunable properties. A range of primary amines, such as aliphatic and benzyl amines, are readily converted with 5-HMF to form the corresponding BHMFA in good yields. The reaction proceeds through reductive amination of 5-HMF with primary amine to form secondary amine, followed by reductive amination of 5-HMF with in situ generated secondary amine to produce BHMFA.
Versatile CO-assisted direct reductive amination of 5-hydroxymethylfurfural catalyzed by a supported gold catalyst
Zhu, Ming-Ming,Tao, Lei,Zhang, Qi,Dong, Jing,Liu, Yong-Mei,He, He-Yong,Cao, Yong
, p. 3880 - 3887 (2017)
Reductive amination (RA) constitutes an attractive and practical strategy for discovering protocols capable of converting biomass into valuable N-containing compounds. Described herein is a versatile and sustainable RA of 5-hydroxymethyl-furfural (HMF), an important biomass-derived aldehyde, using abundant and cheaply available CO and water as reductants. A single phase rutile titania supported gold (Au/TiO2-R) catalyst is shown to efficiently catalyze this CO/H2O-mediated RA under mild and convenient conditions. With this system, a broad spectrum of primary and secondary amines can be used as suitable substrates and the desired reaction can proceed favourably in a highly chemoselective, efficient and atom-economical fashion. In particular, this protocol can also allow convenient access to bis(hydroxylmethylfurfuryl)-amines, a new group of furan-based monomers with great potential to form functional biopolymers with tunable properties. Moreover, this CO-assisted RA is more efficient (higher TON and TOF) and more eco-friendly (increased resource efficiency) than the previous state-of-the-art technique.
Reductive Amination, Hydrogenation and Hydrodeoxygenation of 5-Hydroxymethylfurfural using Silica-supported Cobalt- Nanoparticles
Chandrashekhar, Vishwas G.,Natte, Kishore,Alenad, Asma M.,Alshammari, Ahmad S.,Kreyenschulte, Carsten,Jagadeesh, Rajenahally V.
, (2021/11/30)
Efficient and selective conversion of renewable feedstocks to essential chemicals and fuels applying green and sustainable catalytic processes is of central importance and attracts scientific interest. Among different biomass-based feedstocks, 5-hydroxymethylfurfural (HMF) represents valuable platform compound widely used for the synthesis of valuable chemicals, fuels, and polymers. Here we report cobalt nanoparticles catalyzed reductive amination, hydrogenation and hydrodeoxygenation of HMF to produce furan based primary, secondary and tertiary amines including N-methylamines as well as 2,5-bis(hydroxymethyl)furan, (5-methylfuran-2-yl)methanol and selected N-, O-, and S-containing heterocycles. Key to success for this HMF valorization is the use of reusable silica supported cobalt-based nanoparticles, which have been prepared by the immobilization and pyrolysis of Co-terephthalic acid-piperazine MOF template on silica.
PROCESS FOR PRODUCING AN AMINE IN A SOLVENT SYSTEM CONTAINING WATER
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Page/Page column 18-19, (2019/10/04)
The present invention pertains to a process for producing an amine from an aldehyde or a precursor thereof, or a ketone in a solvent system containing water. The process is more environmentally friendly and permits to obtain an amine compound under mild reaction conditions.
Aryne cycloaddition with 3-oxidopyridinium species
Ren, Hailong,Wu, Chunrui,Ding, Xiuxiu,Chen, Xiaoge,Shi, Feng
supporting information, p. 8975 - 8984,10 (2012/12/12)
The [3 + 2] cycloaddition of arynes with 3-oxidopyridinium species is examined using the Kobayashi benzyne precursor. The reaction affords a bicyclo[3.2.1] skeleton under mild conditions. A [7 + 2] cycloaddition mode with a subsequent pyridine ring-opening event has also been observed.
Production of biobased HMF derivatives by reductive amination
Cukalovic, Ana,Stevens, Christian V.
experimental part, p. 1201 - 1206 (2010/10/20)
5-(Hydroxymethyl)furfural (HMF) has recently attracted a significant amount of revived attention as a renewable building block for conversion to a wide range of useful derivatives. A simple procedure for the conversion of HMF to (5-alkyl- and 5-arylaminomethyl-furan-2-yl)methanol has now been developed. Reactions were conducted without the use of a catalyst and under very mild conditions. As a proof of concept, a small library of derivatives was produced from HMF and several aliphatic and aromatic amines in high yields and requiring only minimal purification. This route presents a novel way for the production of furan-based renewable building blocks. The Royal Society of Chemistry 2010.
