Direct oxidative esterification of toluene with 1,3‐dicarbonyl compounds catalysed by copper complex supported on magnetic nanoparticles

Azizi, Kobra; Esfandiary, Naghmeh; Karimi, Meghdad; Kazemi, Maryam; Heydari, Akbar

doi:10.1002/aoc.3658

Cited by 13 publications

(6 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similarly, in the solid-state, compound 12j (R4-OCH 3 ) exists as an enolic tautomer with an E-geometry of double bonds and the enolic double bond in the Z geometry (Figure ). This result compliments the previous report of a keto form for the same compound (CCDC 1486216) . The six-membered cyclic transition state between the two enolic forms involves an O–H···O hydrogen-bonding interaction with a donor–acceptor distance of 2.5048(15) and an OHO angle of 159(3)°.…”

Section: Computational Results and Discussionsupporting

confidence: 90%

“…Curcumin 1 has been structurally characterized at several temperatures. 32 A total of only nine structural reports exist for curcuminoids contained within this paper: o -OMe 12h (CCDC 841100), 33 p -OH 12m (CCDC 1117584, 1163657, 1867868–1867871), 34 p -OMe 12j (CCDC 1486216), 35 and the unsubstituted aryl ring 12a (CCDC 1123476). 36 These structures all contain the curcuminoid in the enol form.…”

Section: Computational Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

et al. 2022

View full text Add to dashboard Cite

A green and optimized protocol has been developed for the preparation of symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones with modified substrate scope and good functional group tolerance. Syntheses proceed smoothly under solvent-free conditions, providing moderate to excellent product yields with a minimal workup procedure. Control experiments, spectroscopic, and computational studies support a mechanism involving the boron-assisted in situ generation of imine intermediates. Crystal structures of three curcuminoids and isolated mechanistic intermediates are reported. The data provide insight for the further development of solvent-free protocols toward diverse curcumin derivatives in the fields of pharmaceutical and synthetic chemistries.

show abstract

Section: Computational Results and Discussionsupporting

confidence: 90%

Section: Computational Results and Discussionmentioning

confidence: 99%

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Equimolar quantities of Co 2+ , Ni 2+ , and Cu 2+ chlorides (0.5 mmol in 25‐ml ethanol) were added to the ligand of hydrazone ( HL ) (0.5 mmol in 25‐ml ethanol) to make the metal chelates. [ 22 ] The combination was heated and refluxed for 2 h while stirring, then the solids that were formed then filtered out, washed more than a few times in ethanol, and dried. The amount of water required for crystallization was determined via thermogravimetry that will be discussed later.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization, DNA binding, and biological action of dimedone arylhydrazone chelates

El‐Bindary

El-Bindary

2022

Applied Organom Chemis

View full text Add to dashboard Cite

A chain of metal(II) chelates that M = Co2+, Ni2+, and Cu2+ have been produced from 2‐(4‐sulfadiazine)hydrazono dimedone (HL) and characterized on analyses of elemental, Fourier‐transform infrared (FTIR) spectra, electronic, susceptibility to magnetic fields, and molar conductance. The chelates are nonelectrolytes, according to measurements of conductance. Spectroscopy methods and additional analytical measurements detect pseudo octahedral shape of Co2+ and Ni2+ chelates, but square planar structure for Cu2+ chelate. The ligand (HL) acts as a monobasic bidentate ligand by coordinating via oxygen atom of the carbonyl (C═O) group and the nitrogen atom of the hydrazone moiety (NH) with deprotonation. The enhanced, bond angles, bond lengths, and quantum chemical factors were used to determine the ligand and its complexes. Absorption spectra method and measurements of viscosity were used to investigate DNA linking activity. In the viability experiment of vinblastine and colchicine, the findings of synthesized compounds against the human cancer cell lines MCF‐7 and HepG‐2 were reported in contrast to positive controls. The antioxidant function of chelates is resolute by means of the free radical‐scavenging analyze (DPPH). As a final point, the antimicrobial effects of the chelates were studied utilizing the diffusion disc technique on fungal (Candida albicans), gram‐positive (Staphylococcus aureus), and gram‐negative (Escherichia coli) bacteria.

show abstract

“…This intermediate, by adsorbing an electron, turned into benzaldehyde. In the final step, by coupling amine/hydrazine with produced benzaldehyde, the final product was shaped. , …”

Section: Resultsmentioning

confidence: 99%

“…In the final step, by coupling amine/hydrazine with produced benzaldehyde, the final product was shaped. 40,41 Synthesized GO-IL-CO 2 H-Cu catalyst could be used more than five times without noticeable loss of its catalytic activity.…”

Section: Industrial and Engineering Chemistry Researchmentioning

confidence: 99%

Study on Oxidative Condensation of Toluene and Hydrazine/Aniline Catalyzed by Copper Complex Immobilized on Functionalized Graphene Oxide

Zand

Ghafuri

Rashidizadeh

et al. 2019

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

The graphene oxide–imidazolium ionic liquid–CO2H–Cu (GO-IL-CO2H-Cu) catalyst has been successfully synthesized in the present research, and its catalytic activity was studied in a direct oxidative condensation reaction. Also graphene oxide–imidazolium ionic liquid–Cu (GO-IL-Cu), MCM-41–imidazolium ionic liquid–Cu (MCM-41-IL-Cu), MCM-41–imidazolium ionic liquid–CO2H–Cu (MCM-41-IL-CO2H-Cu), chitosan–imidazolium ionic liquid–CO2H–Cu (Chit-IL-CO2H-Cu), and graphitic carbon nitride–imidazolium ionic liquid–CO2H–Cu (g-C3N4-IL-CO2H-Cu) solid substrates were synthesized and used in the oxidative condensation reaction. Obtained results indicated that GO-IL-CO2H-Cu has higher catalytic activity than the other substrates and could be used more than five times without noticeable loss of its catalytic activity. The chemical structure and morphology of synthesized GO-IL-CO2H-Cu were characterized by Fourier transform infrared (FT-IR) spectroscopy, Raman spectroscopy, X-ray diffraction (XRD), energy dispersive X-ray spectroscopy (EDX), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA).

show abstract

Direct oxidative esterification of toluene with 1,3‐dicarbonyl compounds catalysed by copper complex supported on magnetic nanoparticles

Cited by 13 publications

References 24 publications

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

Synthesis, characterization, DNA binding, and biological action of dimedone arylhydrazone chelates

Study on Oxidative Condensation of Toluene and Hydrazine/Aniline Catalyzed by Copper Complex Immobilized on Functionalized Graphene Oxide

Contact Info

Product

Resources

About