Fabrication of heterogeneous-based lacunary polyoxometalates as efficient catalysts for the multicomponent and clean synthesis of pyrazolopyranopyrimidines

Yekke-Ghasemi, Zahra; Heravi, Majid M.; Malmir, Masoumeh; Jahani, Ghazaleh; Bisafar, Masoumeh Bagheri; Mirzaei, Masoud

doi:10.1016/j.inoche.2022.109456

Cited by 37 publications

(13 citation statements)

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“…In line with our investigations on the design, synthesis and computational modeling of heterogeneous catalysts and development of ecologically benign methods for chemical synthesis [34][35][36][37][38][39] regarding the reports of researchers in the field of joining theory and experiments [40][41][42] , we have recently focused on the application of naturalheterogeneous catalysts in several organic conversions 19,[43][44][45] . Hence, we are introducing efficient catalysts using n-HA decoration with organic functionalities and Ag-NPs doping by bio-assisted method.…”

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confidence: 83%

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

Sisakhti

Malmir

Bisafar

et al. 2022

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In the present study, a natural-based heterogeneous catalyst is synthesized. For this purpose, nano-hydroxyapatite (n-HA) is prepared, silica-modified and functionalized with phthalimide. Finally, Ag2+ was immobilized onto n-HA/Si-PA-SC and reduced to Ag nanoparticles by Bellis perennis flowers extract. n-HA/Si-PA-SC@Ag characterized by TGA, FTIR, SEM/EDX, XRD, TEM, BET and ICP-AES techniques. Moreover, metal–ligand interactions in n-HA/Si-PA-SC@Ag complex models were assessed to make a quantitative representation for the immobilization behavior of Ag NPs on the surface of n-HA/Si-PA-SC through quantum chemistry computations. Furthermore, the performance of n-HA/Si-PA-SC@Ag was studied in the nitroarene, methylene blue and congo red reductions. Finally, the recyclability study as well as Ag-leaching verified that, n-HA/Si-PA-SC@Ag was stable and reused-up to four times without losing its activity.

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confidence: 83%

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

Sisakhti

Malmir

Bisafar

et al. 2022

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“…In line with the ongoing research and growing interest in the synthesis and application of heterogeneous catalysts as well as the pursuit of environmentally friendly approaches to enhance chemical reactions, [36][37][38][39][40][41][42][43][44] this study presents a novel method for synthesizing catalysts based on MOFs. The catalyst are prepared by conjucating cyanuric chloride (TCT) and imidazole (IMI) with aspartic acid, which is then decorated with Fe 3 O 4 .…”

Section: Introductionmentioning

confidence: 99%

Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe₃O₄ under mild conditions

Bisafar,

Malmir,

Heravi

2023

J of Chemical Tech & Biotech

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BACKGROUNDToday, studies on the catalytic reduction of nitroarenes and dyes are of crucial because nitroarenes, especially 4‐nitrophenol (4‐NPh) and dyes, which are considered important pollutants in wastewater, can pose risks to humans. It is noteworthy that amines are known as valuable intermediates in many industries, therefore, providing an efficient method to achieve these compounds is necessary to protect the environment. In this project, a magnetic MOFs‐based catalyst (containing Cu species as an active site) was found to offer a unique and cost‐effective route for the catalytic reduction of nitroarene and organic dyes.RESULTSIn this study, a novel magnetic catalyst, Fe3O4@glu/Cu‐TAZ‐IMI, based on MOF was synthesized. The core‐shell structure of Fe3O4@glu, functionalized with aspartic acid with TAZ‐IMI and Cu(OAc)2, resulted in the formation of magnetic MOF structure. The structure of this new nanocomposite was identified by X‐ray diffraction (XRD), Fourier Transform Infrared Spectrometer (FTIR), Brunauer–Emmett–Teller (BET), Scanning electron microscopy/energy dispersive X‐ray (SEM/EDX), Thermogravimetric analysis (TGA), High‐resolution transmission electron microscopy (HRTEM), Value stream mapping (VSM), Raman spectroscopy and Inductively coupled plasma‐optical emission spectrometry (ICP‐OES). The catalytic performance of the synthesized catalyst was evaluated for the reduction of nitro compounds and organic dyes, and the results were validated by Gas chromatography‐mass (GC–MS) and ultraviolet light (UV–Vis) spectroscopy. Moreover, the rate constants for the reduction of 4‐NPh, Congo red (CR), and Methylene blue (MB) followed pseudo first‐order kinetics model, which calculated values of 0.31 min−1, 0.355 min−1 and 0.044 s−1, respectively.CONCLUSIONThe catalytic efficacy of Fe3O4@glu/Cu‐TAZ‐IMI catalyst remained intact during the reduction of nitroarenes and organic dyes in aqueous and mild conditions. The findings demonstrate that this novel heterogeneous mesoporous catalyst exhibits exceptional catalytic activity and remarkable stability towards reduction reactions. Moreover, owning to its thermal and structural stability, the catalyst could be easily magnetically separated, recovered, and reused for up to 10 consecutive cycles without experiencing significant activity decline, effectively preventing the depletion of copper species from its structure. © 2023 Society of Chemical Industry.

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“…Apart from the 3‐substituted indoles, there are several other organic moieties successfully synthesized by MCR protocol using polyoxometalate catalysts like Pyrazolo‐[3,3:5,6]pyrido[2,3‐d]pyrimidine‐diones using Grafted Neodymium Complex of Tungstosilicate, [37] Hantzsch‐Biginelli reactions using Nd−Ag@polyoxometalate, [38] pyrrolo[2,3,4‐kl] acridin‐1‐one using polyoxometalate@lanthanoid, [39] pyrazolopyranopyrimidines using [Ln(W 5 O 18 ) 2 ] 9− , [40,41] chromenopyrimidine‐2,5‐diones using 12‐Tungstoboric acid, [42] spirochromenes using amino acid@isopolyoxometalate [43] and isatin derivatives using La‐ polyoxometalate [44] …”

Section: Introductionmentioning

confidence: 99%

“…[35] Rawat et al have demonstrated that reduced graphene (RGO)/ZnO composites act as highly efficient and reusable heterogeneous catalysts in one pot three-component synthesis of various 3substituted indoles. [36] Apart from the 3-substituted indoles, there are several other organic moieties successfully synthesized by MCR protocol using polyoxometalate catalysts like Pyrazolo- [3,3:5,6]pyrido [2,3-d]pyrimidine-diones using Grafted Neodymium Complex of Tungstosilicate, [37] Hantzsch-Biginelli reactions using NdÀ Ag@polyoxometalate, [38] pyrrolo [2,3,4-kl] acridin-1one using polyoxometalate@lanthanoid, [39] pyrazolopyranopyrimidines using [Ln(W 5 O 18 ) 2 ] 9À , [40,41] chromenopyrimidine-2,5-diones using 12-Tungstoboric acid, [42] spirochromenes using amino acid@isopolyoxometalate [43] and isatin derivatives using Lapolyoxometalate. [44] ZnO is used as a versatile solid catalyst in various multicomponent reactions.…”

Section: Introductionmentioning

confidence: 99%

Selective one pot multicomponent green synthesis of 3‐[(aryl)(arylthio)methyl]‐1H‐indole derivatives utilizing enhanced Lewis acidic sites of Surfactant‐assisted ZnO catalyst

et al. 2023

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Five different ZnO nanocrystallites (ZnO‐1 to ZnO‐5) were successfully synthesized by a surfactant‐assisted hydrothermal technique using various surfactants. All the ZnO nanocrystallites are thoroughly characterized by XRD, IR, UV‐DRS spectroscopy and FESEM‐EDS analysis. Among the synthesized ZnO nanocrystallites, the CTAB‐assisted synthesized ZnO‐4 exhibited a fine disc‐like morphology with a minimum crystallite size (23 nm). Subsequent to reaction optimization studies, the ZnO‐4 is utilized as an efficient catalyst for one pot‐three component green synthesis of 3‐[(aryl)(arylthio)methyl]‐1H‐indoles (4a–4p) via. condensation of a variety of indoles, aromatic aldehydes and aromatic thiols at room temperature in water. The single‐crystal X‐ray structure of 3‐[(phenyl)(phenylthio)methyl]‐1H‐indole (4a) is also been reported (CCDC 2170437). The Lewis acidic property of the catalyst‐supported probable mechanism is well proposed subsequent to pyridine‐IR studies of the ZnO catalysts. Indeed, CTAB‐assisted synthesized ZnO‐4 was found to be most effective and selective Lewis acid catalyst for the synthesis of a variety of 3‐[(aryl)(arylthio)methyl]‐1H‐indole derivatives in water at ambient temperature with merits like higher yields, lower reaction time, catalyst recovery and reuse.

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Fabrication of heterogeneous-based lacunary polyoxometalates as efficient catalysts for the multicomponent and clean synthesis of pyrazolopyranopyrimidines

Cited by 37 publications

References 64 publications

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe₃O₄ under mild conditions

Selective one pot multicomponent green synthesis of 3‐[(aryl)(arylthio)methyl]‐1H‐indole derivatives utilizing enhanced Lewis acidic sites of Surfactant‐assisted ZnO catalyst

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Fabrication of heterogeneous-based lacunary polyoxometalates as efficient catalysts for the multicomponent and clean synthesis of pyrazolopyranopyrimidines

Cited by 37 publications

References 64 publications

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe3O4 under mild conditions

Selective one pot multicomponent green synthesis of 3‐[(aryl)(arylthio)methyl]‐1H‐indole derivatives utilizing enhanced Lewis acidic sites of Surfactant‐assisted ZnO catalyst

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Highly selective reduction of nitro compounds catalyzed by MOF‐derived glucose stabilized Fe₃O₄ under mild conditions