Browse
Submit Data
Databases
API
Help

Dataset Information

28 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Highly Efficient Bifunctional Amide Functionalized Zn and Cd Metal Organic Frameworks for One-Pot Cascade Deacetalization-Knoevenagel Reactions.

ABSTRACT: A pyridine-based amide functionalized tetracarboxylic acid, 5,5'-(pyridine-2, 6-dicarbonyl)bis(azanediyl)}diisophthalic acid (H4L), was synthesized and its coordination chemistry toward zinc(II) and cadmium(II) ions was studied. The reactions of H4L with Zn(NO3)2.6H2O and Cd(NO3)2.4H2O led to its full or partial deprotonation, respectively, and the formation of the 2D coordination polymers [Zn2(L)(H2O)4]n.4n(H2O) (1) and [Cd3(HL)2(DMF)4]n.4n(DMF) (2) (DMF = N,N'-dimethylformamide), respectively. They were characterized by elemental analysis, FT-IR, photoluminescence, thermogravimetry, and single-crystal and powder X-ray diffraction. In 1, the L4- ligand is planar with every carboxylate anion binding a Zn(II) cation and giving rise to a 2D grid with the metals with tetrahedral environments. In 2, the combination of bridging HL3- and dimethylformamide to form trinuclear Cd(II) clusters engenders secondary building block units and generates a layer-type 2D network with the metals with octahedral and pentagonal bipyramid coordination geometries. The topological analyses of 1 and 2 reveal 2,4-connected and 3,6-connected binodal nets, respectively. On account of the presence of Lewis acid (Zn or Cd centers) as well as basic (uncoordinated pyridine and amide groups) sites, 1 and (to a much lower extent) 2 effectively catalyze the one-pot cascade deacetalization-Knoevenagel condensation reactions under quite mild conditions. They act as heterogeneous catalysts, being easy to recover and recycle without losing activity.

SUBMITTER: Karmakar A

PROVIDER: S-EPMC6824099 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Bifunctional Mesoporous Carbon Nitride: Highly Efficient Enzyme-like Catalyst for One-pot Deacetalization-Knoevenagel Reaction.

Project description:Recently, mesoporous carbon nitride (MCN) has aroused extensive interest for its potential applications in organocatalysis, photo- and electrochemistry and CO2 capture. However, further surface functionalization of MCN for advanced nanomaterials and catalysis still remains very challenging. Here we show that acidic carboxyl groups can be smoothly introduced onto the surface of well-ordered MCN without annihilation between the introduced acid groups and MCN's inherent basic groups through a facile UV light oxidation method. The functionalization generates a novel bifunctional nanocatalyst which offers an enzyme-like catalytic performance in the one-pot deacetalization-Knoevenagel reaction of benzaldehyde dimethylacetal and malononitrile with 100% conversion and more than 99% selectivity due to the cooperative catalysis between the acid and base groups separated on the surface of the catalyst. The results provide a general method to create multifunctional nanomaterials and open new opportunities for the development of high efficient catalyst for green organic synthesis.

| S-EPMC4525375 | biostudies-literature

A post-sulfonated one-pot synthesized magnetic cellulose nanocomposite for Knoevenagel and Thorpe-Ziegler reactions.

Project description:The development of biodegradable and active cellulosic-based heterogeneous catalysts for the synthesis of different organic compounds would be attractive in pharmaceutical and petrochemical-related industries. Herein, a post-sulfonated composite of one-pot synthesized magnetite (Fe3O4) and cellulose nanocrystals (CNCs) was used as an effective and easily separable heterogeneous catalyst for activating the Knoevenagel and Thorpe-Ziegler reactions. The composite was developed hydrothermally from microcrystalline cellulose (MCC), iron chlorides, urea, and hydrochloric acid at 180 °C for 20 h in a one-pot reaction. After collecting the magnetic CNCs (MCNCs), post-sulfonation was performed using chlorosulfonic acid (ClSO3H) in DMF at room temperature producing sulfonated MCNCs (SMCNCs). The results confirmed the presence of sulfonated Fe3O4 and CNCs with a hydrodynamic size of 391 nm (±25). The presence of cellulose was beneficial for preventing Fe3O4 oxidation or the formation of agglomerations without requiring the presence of capping agents, organic solvents, or an inert environment. The SMCNC catalyst was applied to activate the Knoevenagel condensation and the Thorpe-Ziegler reaction with determining the optimal reaction conditions. The presence of the SMCNC catalyst facilitated these transformations under green procedures, which enabled us to synthesize a new series of olefins and thienopyridines, and the yields of some isolated olefins and thienopyridines were up to 99% and 95%, respectively. Besides, the catalyst was stable for five cycles without a significant decrease in its reactivity, and the mechanistic routes of both reactions on the SMCNCs were postulated.

| S-EPMC10517101 | biostudies-literature

A facile, rapid procedure for Knoevenagel condensation reaction catalyzed by efficient amino-bifunctional frameworks under mild conditions.

Project description:A series of bifunctional hexagonal MOFs have been successfully constructed by the introduction of various amine functional groups within the unsaturated Cu-based MOF, HKUST, to access amino-modified frameworks. The prepared compounds are cost-effective and display high chemical and thermal stability. They were effectually exploited as efficacious and superb heterogeneous catalysts in rapid and facile Knoevenagel condensation reactions for a variety of substrates containing different electron-donating and electron-withdrawing substituents with very high conversion, good reusability under mild conditions, and very short reaction time. The contaminant presence of Lewis acid and basic sites resulted in efficient condensation reactions by the prepared catalysts.

| S-EPMC10511422 | biostudies-literature

Mesitylene Tribenzoic Acid as a Linker for Novel Zn/Cd Metal-Organic Frameworks.

Project description:Three new Metal-Organic Frameworks, containing mesitylene tribenzoic acid as a linker and zinc (1) or cadmium as metals (2,3), were synthesized through solvothermal reactions, using DMF/ethanol/water as solvents, at temperatures of 80 °C (structures 1 and 3) and 120 °C (structure 2). Following single-crystal X-ray diffraction, it was found that 1 and 3 crystallize in the P21/c and C2/c space groups and form 2D networks, while 2 crystallizes in the Fdd2 space group, forming a 3D network. All three frameworks, upon heating, were found to be stable up to 350 °C. N2 sorption isotherms revealed that 1 displays a BET area of 906 m2/g. Moreover, the porosity of this framework is still present after five cycles of sorption/desorption, with a reduction of 14% of the BET area, down to 784 m2/g, after the fifth cycle. The CO2 loading capacity of 1 was found to be 2.9 mmol/g at 0 °C.

| S-EPMC9227569 | biostudies-literature

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides.

Project description:A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

| S-EPMC5815282 | biostudies-other

Cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: the amide question.

Project description:The n-butyramido, isobutyramido, benzamido, and furancarboxamido functions profoundly modulate the electronics of the stilbene olefinic and NH groups and the corresponding radical cations in ways that influence the efficiency of the cyclization due presumably to conformational and stereoelectronic factors. For example, isobutyramido- stilbene undergoes FeCl(3) promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.

| S-EPMC6264379 | biostudies-literature

Anionic cascade reactions. One-pot assembly of (Z)-chloro-exo-methylenetetrahydrofurans from β-hydroxyketones.

Project description:The assembly of (Z)-chloro-exo-methylenetetrahydrofurans by an original and connective anionic cascade sequence is reported. Base-catalysed condensation of β-hydroxyketones with 1,1-dichloroethylene generates, in moderate to good yields, the corresponding (Z)-chloro-exo-methylenetetrahydrofurans. Acidic treatment of this motif leads to several unexpected dimers, possessing unique structural features.

| S-EPMC3701418 | biostudies-literature

Synergistic Degradation of a Hyperuricemia-Causing Metabolite Using One-Pot Enzyme-Nanozyme Cascade Reactions.

Project description:Multi-enzyme cascade reactions are frequently found in living organisms, in particular when an intermediate should be eliminated. Recently, enzyme-mimic nanomaterials (nanozymes) received much attention for various applications, because they are usually more stable and cost-effective than enzymes. However, enzyme-nanozyme cascade reations have not been yet extensively exploited. Therefore, in this study, we investigated one-pot enzyme-nanozyme cascade reactions using urate oxidase (UOX) and catalase-mimic gold nanoparticle nanozyme (AuNP) with the ultimate goal of treatment of hyperuricemia. UOX degrades hyperuricemia-causing uric acid, but also generates hydrogen peroxide raising several health concerns. We successfully demonstrated that one-pot UOX-AuNP cascade systems degrade uric acid more than five times faster than UOX alone, by eliminating potentially cytotoxic hydrogen peroxide, similar to enzyme-enzyme reactions.

| S-EPMC5347090 | biostudies-literature

Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

Project description:A post-Ugi diastereoselective one-pot cascade reaction requiring no metal catalyst was developed. The reaction scope was wide with mild conditions and good yields. A collection of spiroindolines was prepared by the protocol and screening tests in several difficult-to-inhibit cancer cell lines were conducted. The relationship of structure and anticancer activities was promising and in the Huh7 cell lines compound 16 j is more potent than Vinbalstine. The cyclization design strategy could be applicable to other multicomponent reactions (MCRs) for synthesizing bioactive and drug-like heterocycles.

| S-EPMC6042644 | biostudies-literature

Constructing new metal-organic frameworks with complicated ligands from "One-Pot" <i>in situ</i> reactions.

Project description:Metal-organic frameworks (MOFs) have emerged as one of the most fascinating libraries of porous materials. In spite of their myriad merits, practical application of most MOFs is restricted due to their high preparation cost because of the complicated organic ligands involved. To address this limitation, we propose to use simple and cheap organic precursors to synthesize MOFs with complicated ligands via "one-pot" in situ reactions of these precursors along with the formation of new MOFs. In this work, we have carefully screened several organic reactions, through which target ligands were generated in situ from easily available reactants during the MOF construction. With this "one-pot" approach, the fabrication of a series of novel MOFs by integrating the organic covalent bond and the coordinate bond has thus been realized through the judicious selection of organic reactions, which effectively simplifies the MOF synthesis process and thus reduces the cost.

| S-EPMC6461020 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data