Fe3O4@C@OSO3H as an efficient, recyclable magnetic nanocatalyst in Pechmann condensation: green synthesis, characterization, and theoretical study

Samiei, Zahra; Soleimani‐Amiri, Somayeh; Azizi, Zahra

doi:10.1007/s11030-019-10025-w

Cited by 32 publications

(25 citation statements)

References 67 publications

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“…The FT‐IR spectra of Fe 3 O 4 @CONa displayed a broad absorption at 3,420 cm −1 corresponding to the stretching vibrations of remaining OH on the surface of nanoparticles (Figure 4). [ 41,43,48 ] Also, signals of 2,923 and 2,856 cm −1 were related to CH stretching vibrations. The absorptions of 1,600–1,300 cm −1 and 1,000–1,100 cm −1 were assigned to CC and CO stretching vibrations, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…[48] At the first step, Fe 3 O 4 @C was produced using inexpensive and accessible reactants by solvothermal procedure. [41,43,48] At the second step, sodium hydroxide was added to mixture of well-dispersed Fe 3 O 4 @C in distilled water under stirring to give Fe 3 O 4 @CONa (Scheme 1). The produced Fe 3 O 4 @CONa was considered and confirmed using Fourier transform infrared (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), and vibrating sample magnetometer (VSM) analyses.…”

Section: Preparation and Characterization Of Fe 3 O 4 @Conamentioning

confidence: 99%

“…At first Fe 3 O 4 @C was synthesized by an improved solvothermal procedure. [41,43,48] Then produced Fe 3 O 4 @C was converted to Fe 3 O 4 @C@ONa with NaOH solution (17.5 M) at 70 C. [48] The created Fe 3 O 4 @C@ONa was removed by an external magnet with basic character of about 2 mmol/g.…”

Section: Preparation Of Fe 3 O 4 @C@onamentioning

confidence: 99%

“…[28][29][30][31][32] Nowadays with the advancement of nanoscience, magnetic nanoparticles (MNPs) as an effective heterogeneous catalyst have been widely synthesized and used efficiently in various organic syntheses. [33][34][35][36][37][38][39][40][41] In addition to common properties of all nanoparticles such as the high surface area, as well as chemical and thermal stability, MNPs could be separated easily from reaction mixture using an external magnet. Immobilization of various shells such as silica and carbon on the surface of MNPs protects them against agglomeration and improves the chemical stability of MNps from environmental degradation and also provide an appropriate surface for further modification while the magnetic core causes easy separation using an external magnet.…”

Section: Introductionmentioning

confidence: 99%

“…[48] Moreover, a theoretical mechanistic study of the reactions could be very essential for designing the desired products and it seems also necessary for deep understanding of how to do the reaction. [41,[49][50][51][52][53][54][55][56][57] Accordingly, the mechanism of 4H-chromene synthesis was investigated by density functional theory (DFT) calculations to explore how to do the reaction of salicylaldehydes (1), active methylenes (2), and carbon base nucleophiles (3). This study could predict the most likely mechanism, rate, and intermediates of the reactions and also this could be a great help in designing new 4H-chromene derivatives.…”

Section: Introductionmentioning

confidence: 99%

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New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Ghavidel

Mirza

Soleimani‐Amiri

et al. 2020

J Chinese Chemical Soc

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A green synthesis of functionalized 4H-chromenes using one-pot, threecomponent reaction of salicylaldehyde (1), active methylene (2), and carbonbased nucleophile (3) using Fe 3 O 4 @CONa nanoparticles in water has been performed at 60 C. The Fe 3 O 4 @CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst and solvent, short reaction time, high product yields, as well as simple work-up procedure were found as some advantages of this methodology. The density functional theory calculations were applied to all-inclusive perception of the one-pot, three-component reaction mechanism. The most reactions progressed through the following route: (a) nucleophilic addition of 2 to 1; (b) ring closing, dehydration; (c) nucleophilic substitution of 3 (2-naphtol, 4-hydroxycumarin) to intermediate. Sometimes mechanism mutated to: (a) nucleophilic addition of 3 (indole, 2-methylindole) to 1, and dehydration; (b) nucleophilic addition of 2 to intermediate; and (c) ring closing, and dehydration. The frontier molecular orbitals, NBO analyses, molecular electrostatic potential of reactants, and intermediates confirmed the proposal mechanisms. Theoretical study could be so helpful to pick out suitable reactants of the reaction.

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Section: Resultsmentioning

confidence: 99%

Section: Preparation and Characterization Of Fe 3 O 4 @Conamentioning

confidence: 99%

Section: Preparation Of Fe 3 O 4 @C@onamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Ghavidel

Mirza

Soleimani‐Amiri

et al. 2020

J Chinese Chemical Soc

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Fe₃O₄@C@prNHSO₃H: A novel magnetically recoverable heterogeneous catalyst in green synthesis of diverse triazoles

Nasehi

Mirza

Soleimani‐Amiri

2021

J Chinese Chemical Soc

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The core–shell magnetic nano‐catalyst of Fe3O4@C@PrNHSO3H was proposed, synthesized, and fully described by transmission electron microscopy, field‐emission scanning electron microscope, energy‐dispersive X‐ray, vibrating sample magnetometer, thermal gravimetric analysis, X‐ray diffraction, Fourier transform infrared, and X‐ray photoelectron spectroscopy analysis. Nontoxic texture, magnetic recovery capability, high thermal stability as well as low‐cost synthesis method were found as the unique features of the synthesized core–shell magnetic nano‐catalyst. Fe3O4@C@PrNHSO3H NPs were introduced as a modern magnetic heterogeneous catalyst in the solvent‐free synthesis of triazole derivatives through one‐pot, three‐component condensation of aldehyde, ammonium acetate, and nicotinic hydrazide. The pleasant yield of products, straightforward work‐up, mild reaction conditions, along with magnetically recoverable catalyst were enumerated as the most important advantages of the method. The Fe3O4@C@PrNHSO3H could be easily separated from the reaction mixture by an external magnet and reused six times with the desired catalytic activity.

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Synthesis and Biological Properties of Coumarin Derivatives. A Review

et al. 2021

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Coumarin and its derivatives are widely used as scaffolds in the synthesis of new heterocyclic systems. This review focuses on current developments in the synthesis of heterocyclic coumarin compounds. Numerous approaches especially involving nanoparticle catalysts have been developed to get new bioactive coumarin derivatives endowed with pharmacological and biological activities. The present work describes the reactivity and the new strategies using various catalysts for the synthesis of coumarin and its derivatives reported in the literature and their biological properties.

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Fe3O4@C@OSO3H as an efficient, recyclable magnetic nanocatalyst in Pechmann condensation: green synthesis, characterization, and theoretical study

Cited by 32 publications

References 67 publications

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Fe₃O₄@C@prNHSO₃H: A novel magnetically recoverable heterogeneous catalyst in green synthesis of diverse triazoles

Synthesis and Biological Properties of Coumarin Derivatives. A Review

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Fe3O4@C@OSO3H as an efficient, recyclable magnetic nanocatalyst in Pechmann condensation: green synthesis, characterization, and theoretical study

Cited by 32 publications

References 67 publications

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Fe3O4@C@prNHSO3H: A novel magnetically recoverable heterogeneous catalyst in green synthesis of diverse triazoles

Synthesis and Biological Properties of Coumarin Derivatives. A Review

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Fe₃O₄@C@prNHSO₃H: A novel magnetically recoverable heterogeneous catalyst in green synthesis of diverse triazoles