Template-directed approach to solid-phase combinatorial synthesis of furan-based libraries

Gupta, Prem K.; Singh, Sanjay Kumar; Pathak, Arunendra; Kundu, Bijoy

doi:10.1016/s0040-4020(02)01396-0

Cited by 31 publications

(13 citation statements)

References 19 publications

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“…One example of obtaining these compounds from HMF was published by Gupta et al 42 Using a template directed approach and solid-phase catalysis, a library of similar heterocyclic compounds was synthesized starting from resin-immobilized HMF. In an automated synthesizer, more than fifty compounds were produced with purities of 70-92% but in rather modest yields.…”

Section: Introductionmentioning

confidence: 99%

Production of biobased HMF derivatives by reductive amination

Cukalovic

Stevens

2010

Green Chem.

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5-(Hydroxymethyl)furfural (HMF) has recently attracted a significant amount of revived attention as a renewable building block for the conversion to a wide range of useful derivatives. A simple procedure for the conversion of HMF to (5-alkylaminomethyl-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

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Section: Introductionmentioning

confidence: 99%

Production of biobased HMF derivatives by reductive amination

Cukalovic

Stevens

2010

Green Chem.

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“…It can serve as a precursor to numerous products and chemical intermediates relevant to the fuel, polymer, and pharmaceutical industries [4][5][6][7][8][9]. Selective hydrogenation gives a fuel additive with combustion properties similar to ethanol, and superior diesel miscibility [10].…”

Section: Introductionmentioning

confidence: 99%

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

et al. 2010

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Solid catalysts based on SBA-15 silica were designed for the conversion of fructose to 5-hydroxymethylfurfural (HMF). The catalysts incorporate thioether groups that may promote the tautomerization of fructose to its furanose form, as well as sulfonic acid groups to catalyze its dehydration. The materials were characterized by elemental analysis, X-ray diffraction, N 2 adsorption/ desorption, and solid-state 13 C and 29 Si CP/MAS NMR spectroscopy. Functional groups incorporated into mesoporous silica by co-condensation are more robust under the reaction conditions (water at 180°C) than those grafted onto a non-porous silica. The bifunctional mesoporous catalyst achieved a selectivity for HMF of 74% at 66% fructose conversion.

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“…Kundu and coworkers loaded HMF onto Sieber amide resin via the formation of amide and ester bonds using aliphatic dicarboxylic acid anhydride (Scheme 68). [200] The resin-supported HMFs 174 could be engaged in multicomponent A 3 couplings to provide, after separation from the solid support, propargylamines 175. Other multi-step transformations giving access to diverse nitrogen-containing heterocycles such as 176 and 177 were also successfully implemented using this supported synthesis strategy.…”

Section: Scheme 67 Ugi/diels-alder Tandem Reactionmentioning

confidence: 99%

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

Fan

Verrier

Queneau

et al. 2019

COS

104

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Background: 5-Hydroxymethylfurfural (5-HMF) is a biomass-derived platform chemical, which can be produced from carbohydrates. In the past decades, 5- HMF has received tremendous attention because of its wide applications in the production of various value-added chemicals, materials and biofuels. The manufacture and the catalytic conversion of 5-HMF to simple industrially-important bulk chemicals have been well reviewed. However, employing 5-HMF as a building block in organic synthesis has never been summarized exclusively, despite the rapid development in this area. Objective: The aim of this review is to bring a fresh perspective on the use of 5-HMF in organic synthesis, to the exclusion of already well documented conversion of 5-HMF towards relatively simple molecules such as 2,5-furandicarboxylic acid, 2,5-dimethylfuran and so on notably used as monomers or biofuels. Conclusion: As it has been shown throughout this review, 5-HMF has been the object of numerous studies on its use in fine chemical synthesis. Thanks to the presence of different functional groups on this platform chemical, it proved to be an excellent starting material for the preparation of various fine chemicals. The use of this C-6 synthon in novel synthetic routes is appealing, as it allows the incorporation of renewable carbonsources into the final targets.

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Template-directed approach to solid-phase combinatorial synthesis of furan-based libraries

Cited by 31 publications

References 19 publications

Production of biobased HMF derivatives by reductive amination

Production of biobased HMF derivatives by reductive amination

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

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