Synthesis of Biologically Active Chalcon Analogues via Claisen-Schmidt Condensation in Solvent-Free Conditions: Supported Mixed Addenda Heteropoly Acid as a Heterogeneous Catalyst

Rafiee, Ezzat; Rahimi, Farzaneh

doi:10.4067/s0717-97072013000300029

Cited by 11 publications

(8 citation statements)

References 23 publications

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“…Recently, immobilising HPA on other solid supports has been demonstrated to be very promising to address this issue. Numerous types of supports including silica [2][3][4][5][6][7][8][9][10][11][12][13], titania [14][15][16], zeolites (Y, USY) [17][18][19], mesoporous materials (SBA-15, MCM-41) [20][21][22][23], carbon [24][25][26] and graphene oxide [27] have been used to immobilise HPA by encapsulation, tethering and grafting routes. For example, Mukai et.…”

Section: Introductionmentioning

confidence: 99%

Study on the HPA immobilisation on Al-SBA-15 support over Brønsted groups

Truong

Cuong

Mai

et al. 2019

Molecular Catalysis

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In this article, a significant aspect of Brønsted groups in the preparation of HPA/Al-SBA-15 catalyst by immobilising heteropoly acid H3PW12O40 (HPA) to mesoporous Al-SBA-15 support was studied. The crucial factors affected the preparation such as functional groups formed on the support, the use of HPA type for the immobilisation (commercial catalyst or in-situ synthetic HPA), and Si/Al molar ratio of Al-SBA-15 were systematically investigated. The prepared catalysts were tested their performance in polar reagent reactions (fructone synthesis was chosen as an example) to show the effect of HPA after the immobilisaton. Here we tested the HPA content (by Energy-dispersive X-ray method), 2 acidity (by temperature-programmed desorption of ammonia method) and the ethyl acetoacetate conversion in fructone synthesis to prove this concept. The other characterisation methods such as small angle x-ray scattering, Fourier-transform infrared spectroscopy, specific surface area and pore volume also showed the properties change of materials before and after HPA immobilisation. It was shown that the HPA/Al-SBA-15 sample prepared by using HPA commercial catalyst and NH4 + ion-exchanged Brønsted groups of mesoporous Al-SBA-15 support (Si/Al molar ratio of 15) showed the highest acidity and catalytic activity (ethyl acetoacetate conversion of 93.49 wt%) in comparison to HPA commercial catalyst as well as to the other catalysts. In addition, this catalyst also showed good catalytic stability after five reaction cycles with slightly reduction of activity, suggesting the prospect of employing HPA/Al-SBA-15 catalyst for organic synthesis of polar compounds.

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Section: Introductionmentioning

confidence: 99%

Study on the HPA immobilisation on Al-SBA-15 support over Brønsted groups

Truong

Cuong

Mai

et al. 2019

Molecular Catalysis

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“…However, there are only a few reports of synthesizing pyrazolyl chalcones using HPAs. 39 Prompted by all these observations, we herein report an easy synthesis of copper-doped phosphotungstic acid which was supported on silica gel by an impregnation method (CuPTA/ SiO 2 ) and employed as a catalyst for Claisen−Schmidt condensation.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Application of Silica-Supported Copper-Doped Phosphotungstic Acid in Claisen–Schmidt Condensation

Siddiqui

Khan

Siddiqui

2017

ACS Sustainable Chem. Eng.

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An efficient, novel, and recyclable silicasupported copper-doped phosphotungstic acid (CuPTA/ SiO 2 ) has been synthesized by an impregnation method. The catalyst has been characterized by FTIR, XRD, SEM/ EDX, ICP−AES, EPR, XPS, and NH 3 -TPD analyses. The catalytic application of the catalyst has been explored for Claisen−Schmidt condensation. The catalyst could be recycled for six runs without any appreciable loss in catalytic activity. The catalytic activity of the recovered catalyst after six runs was confirmed by FTIR, XRD, SEM/EDX, ICP−AES, and EPR analyses. The Claisen−Schmidt products were obtained in excellent yield in a shorter time period.

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“…The mixture was stirred overnight at room temperature, followed by drying using a rotary evaporator [30][31][32].…”

Section: Preparation Of Mo 10 Vmentioning

confidence: 99%

Fe3O4@OA–Pd and Mo10V2@NSiO2 nanoparticles: an efficient and reusable catalytic system for Heck reaction under ligand free conditions

Rafiee

Kahrizi

2015

Res Chem Intermed

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This paper reports the use of a novel catalytic system composed of H 5 PMo 10 V 2 O 40 supported on nano silica (Mo 10 V 2 @NSiO 2 ) and palladium-deposited, oleic-acid-coated Fe 3 O 4 (Fe 3 O 4 @OA-Pd) nanoparticles, as reusable catalysts for Heck coupling reaction under ligand and base free conditions. The average particle size of catalyst was measured to be about 9 nm by transmission electron microscopy. The immobilized palladium on oleic acid coated Fe 3 O 4 was found to be effective in the Heck arylation of various aryl bromides and especially less reactive aryl chlorides with styrene in the presence of heteropoly acid. This method has the advantages of high yields, elimination of ligand and base, simple methodology and easy workup. Interestingly, the novel catalytic system could be recovered in a facile manner from the reaction mixture and recycled several times without any significant loss in catalytic activity. Structural changes of recovered Mo 10 V 2 @NSiO 2 and Fe 3 O 4 @OA-Pd were investigated before reusing for the next runs. Finally, synchronized reusability of both components of our catalytic system has been investigated in the model reaction.

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Synthesis of Biologically Active Chalcon Analogues via Claisen-Schmidt Condensation in Solvent-Free Conditions: Supported Mixed Addenda Heteropoly Acid as a Heterogeneous Catalyst

Abstract: Biologically active chalcones were synthesized via Claisen-Schmidt condensation of aldehydes with different ketones in solvent-free conditions using H 5 PMo 10 V 2 O 40 supported on SiO 2 as a reusable heterogeneous catalyst with excellent reusability.

Cited by 11 publications

References 23 publications

Study on the HPA immobilisation on Al-SBA-15 support over Brønsted groups

Study on the HPA immobilisation on Al-SBA-15 support over Brønsted groups

Synthesis, Characterization, and Application of Silica-Supported Copper-Doped Phosphotungstic Acid in Claisen–Schmidt Condensation

Fe3O4@OA–Pd and Mo10V2@NSiO2 nanoparticles: an efficient and reusable catalytic system for Heck reaction under ligand free conditions

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