Exploration of the Role of Double Schiff Bases as Catalytic Intermediates in the Knoevenagel Reaction of Furanic Aldehydes: Mechanistic Considerations

Schijndel, Jack van; Canalle, Luiz Alberto; Molendijk, Dennis; Meuldijk, J.

doi:10.1055/s-0037-1610235

Cited by 14 publications

(22 citation statements)

References 34 publications

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“…This discovery later led to more evolved condensation reactions, which made use of solventfree reactions catalyzed by ammonium salts, such as ammonium bicarbonate. With this improvement, the carbon-carbon bond creation through a Knoevenagel condensation can withstand the most fierce critique of present-day environmentally challenging times (47,60).…”

Section: Ammoniamentioning

confidence: 99%

“…Recent studies show that the use of ammonia (often from an ammonium salt precursor) results in an exceptionally low E-factor. For instance, the use of ammonium bicarbonate yields an E-factor of 0.3 (47). The calculation for this Knoevenagel condensation reaction is as follows: E-factor equals [((0.80 g diethyl malonate + 0.48 g furanic aldehyde + 0.0395 g ammonium bicarbonate) -1.024 g product) / 1.024 g product].…”

Section: E-factor Calculation For Ammoniamentioning

confidence: 99%

“…The primary amines produce Schiff-base intermediates. For completion, ammonia is taken into account, which establishes a double-Schiff-base in its reaction mechanism (46,47). Scheme 6 shows an overview of the catalytic intermediates of all the suitable amines.…”

Section: Different Amines Introduce Different Knoevenagel Reactionsmentioning

confidence: 99%

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The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

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113

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The formation of carbon-carbon bonds is a quest that has required a lot of research throughout the last 125 years of history of chemistry. The creation of these bonds is key to producing a wide variety of advanced products with great societal importance. In the past, the Knoevenagel reaction entailed a big part of these reactions. All the Knoevenagel reactions are performed with nitrogen-based catalysts, categorized as tertiary amines, secondary amines, primary amines, and ammonium salts. These catalysts operate through different reaction paths, with very deviant intermediates concerning each category. Subsequently, these intermediates create new research opportunities considering their catalytic activity. Some remarks are made in the context of green chemistry, with quantitative analysis using e-factor calculations. In this perspective, the importance of Knoevenagel chemistry exemplified, which is repeatedly overlooked throughout history.

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Section: Ammoniamentioning

confidence: 99%

Section: E-factor Calculation For Ammoniamentioning

confidence: 99%

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The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

Self Cite

113

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“…For example, the reaction of 5-HMF with malonic acid in the presence of ammonium bicarbonate without solvent at 50 ºC afforded the product 35 in 93% yield. [55] Decarboxylation took place at a higher temperature in pyridine, leading to the acrylic acid 36 up to 88% yield. [28,34] Finally, Knoevenagel condensation of the dione 37 promoted by piperidine allowed the preparation of the dihydrochromone 38 which could be rapidly converted into the chromone 39, a photo-activable fluorophore (Scheme 12).…”

Section: Scheme 11 Condensation Of Cyclic Activated Methylene Derivamentioning

confidence: 99%

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

Fan

Verrier

Queneau

et al. 2019

COS

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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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“…[ 9,10 ] The synthesis of macrocyclic complexes [ 2,11–14 ] has continuously investigated due to their applications in fundamental and applied sciences [ 14–16 ] and a huge impact on cancer chemotherapy due to their anticancer activity [ 1,2 ] and in the coordination chemistry. [ 17,18 ]…”

Section: Introductionmentioning

confidence: 99%

Structural characterization, spectroscopic studies, and molecular docking studies on metal complexes of new hexadentate cyclic peptide ligand

Moustafa

Sabry

Zayed

et al. 2021

Applied Organom Chemis

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New cyclic peptide ligand (L), 4,7,17,20‐tetrabenzyl‐2,5,8,16,19,22‐hexaoxo‐3,6,9,15,18,21‐hexaaza‐1(1,3)‐benzenacyclodocosaphane‐10‐carboxylic acid (BOABCA), was prepared using the recommended method. The ligand (L) and its complexes have been proven by using elemental analyses, molar conductivity, and magnetic moment measurements. The structural properties of the title compounds were explored using spectroscopy (1H NMR, ultraviolet [UV]–visible, and Fourier transform infrared [FT‐IR]) and mass spectrometry. The thermal decomposition of the ligand and its complexes are measured by thermal analysis (thermogravimetry [TG] and derivative thermogravimetry [DTG]) technique. The ligand (L) acts as neutral hexadentate with NNOOOO coordination sites and coordinating to the metal ions via the two nitrogen and four oxygen atoms. Bond lengths, bond angles, and quantum chemical characteristics have been established for the ligand and its complexes. The scanning electron microscope (SEM) analysis confirmed the presence of Fe(III) and Ni(II) complexes in nanostructure. The structural formula for the examined cyclic peptide ligand was optimized using Gaussian09 program. The energy gaps and other relevant theoretical parameters were computed applying the DFT/B3LYP technique. Antibacterial properties of the BOABCA ligand (L) and its transition metal complexes have been evaluated. In vitro biological properties for BOABCA ligand (L) and its transition metal complexes were carried out against Gram(+) bacteria (Bacillis subtilis and Staphylococcus aureus) and Gram(−) bacteria (Escherichia coli and Pseudomonas aeruginosa) employing agar diffusion method. The results showed that title compounds are biologically active than the parent BOABCA ligand. Molecular docking has shown favorable interaction between the title compounds and crystal structure of 3t88‐E. coli, 3ty7‐S. aureus, 5h67‐B. subtilis, and 5i39‐P. aeruginosa receptors.

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Exploration of the Role of Double Schiff Bases as Catalytic Intermediates in the Knoevenagel Reaction of Furanic Aldehydes: Mechanistic Considerations

Cited by 14 publications

References 34 publications

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

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

Structural characterization, spectroscopic studies, and molecular docking studies on metal complexes of new hexadentate cyclic peptide ligand

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