One-pot synthesis of pyran derivatives using silica-coated magnetic nanoparticles functionalized with piperidinium benzene-1,3-disulfonate as a new efficient reusable catalyst

Ghorbani‐Vaghei, Ramin; Izadkhah, Vida; Mahmoodi, Jafar

doi:10.1007/s11164-016-2762-x

Cited by 9 publications

(9 citation statements)

References 49 publications

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“…Initially, Fe 3 O 4 MNPs were produced and then coated with SiO 2 through a modified Stöber method . Then, the obtained Fe 3 O 4 @SiO 2 (2.0 g) was dispersed in dry toluene (30 ml) for 30 min, and compound 3 (0.5 g) was added to it (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

“…Initially, Fe 3 O 4 MNPs were produced and then coated with SiO 2 through a modified Stöber method. [23] Then, the obtained Fe 3 O 4 @SiO 2 (2.0 g) was dispersed in dry toluene (30 ml) for 30 min, and compound 3 (0.5 g) was added to it (Scheme 2). The mixture was heated under nitrogen atmosphere and reflux condition for 48 h. Afterwards, the crude Fe 3 O 4 @SiO 2 -HMTA was separated using an external magnet, washed well with EtOH three times and dried within 8 h in an oven.…”

Section: Preparation Of Fe 3 O 4 @Sio 2 -Hmta-so 3 H Mnpsmentioning

confidence: 99%

“…The surfaces of MNPs have been modified with various organic and inorganic compounds such as Co(II) complex, ionic liquids, Schiff base dioxo‐molybdenum(VI), Schiff base complex with histidine, O ‐methyl‐β‐cyclodextrin, oleic acids, and so on. Following our previous research, herein we report the surface modification of silica‐coated MNPs with hexamethylenetetramine (HMTA), which were then sulfonated. To study the catalytic activity of the obtained MNPs, they were used in the synthesis of pyranopyrazole derivatives.…”

mentioning

confidence: 99%

“…[14] Due to the increasing consideration for the use of nanomagnetic catalysts in organic syntheses, [15][16][17][18] efforts have been made to modify the surface of MNPs for increasing their catalytic efficiency. [19,20] The surfaces of MNPs have been modified with various organic and inorganic compounds such as Co(II) complex, [21,22] ionic liquids, [23,24] Schiff base dioxo-molybdenum(VI), [25] Schiff base complex with histidine, [26] O-methyl-β-cyclodextrin, [26] oleic acids, [27] and so on. Following our previous research, [28][29][30][31] herein we report the surface modification of silica-coated MNPs with hexamethylenetetramine (HMTA), which were then sulfonated.…”

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confidence: 99%

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Preparation and characterization of hexamethylenetetramine‐functionalized magnetic nanoparticles and their application as novel catalyst for the synthesis of pyranopyrazole derivatives

Ghorbani‐Vaghei

Izadkhah

2017

Applied Organom Chemis

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A new magnetic catalyst was prepared through the reaction of silanol groups, on the surface of silica‐coated Fe3O4 magnetic nanoparticles, with (3‐chloropropyl)triethoxysilane followed by hexamethylenetetramine and chlorosulfonic acid. The obtained magnetic catalyst was characterized using thermogravimetric analysis, vibrating sample magnetometry, scanning electron microscopy and energy‐dispersive X‐ray analysis. Its catalytic activity was investigated in the synthesis of pyranopyrazole compounds, and the results were excellent regarding high yield of the products and short reaction time.

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Section: Methodsmentioning

confidence: 99%

Section: Preparation Of Fe 3 O 4 @Sio 2 -Hmta-so 3 H Mnpsmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Preparation and characterization of hexamethylenetetramine‐functionalized magnetic nanoparticles and their application as novel catalyst for the synthesis of pyranopyrazole derivatives

Ghorbani‐Vaghei

Izadkhah

2017

Applied Organom Chemis

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“…For instance, sulfonic acid groups are inserted in the IL structure using the sulfonating agents such as 1,3‐Propane sultone and 1,4‐Butane sultone . In addition to imidazole, for the preparation of silica immobilized ILs, piperidine, substituted pyridine, triazole and N,N‐dimethylaminopyridine are used. It is worth to note that silica supported ILs can be prepared in the form of quaternary ammonium salts .…”

Section: Conventional Fss: Types and Their Chemical Modificationsmentioning

confidence: 99%

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Antony

Marimuthu

Yang

et al. 2019

The Chemical Record

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Heterogeneous catalysis plays a key role in promoting green chemistry through many routes. The functionalizable reactive silanols highlight silica as a beguiling support for the preparation of heterogeneous catalysts. Metal active sites anchored on functionalized silica (FS) usually demonstrate the better dispersion and stability due to their firm chemical interaction with FSs. Having certain functional groups in structure, FSs can act as the useful catalysts for few organic reactions even without the need of metal active sites which are termed as the covetous reusable organocatalysts. Magnetic FSs have laid the platform where the effortless recovery of catalysts is realized just using an external magnet, resulting in the simplified reaction procedure. Using FSs of multiple functional groups, we can envisage the shortened reaction pathway and, reduced chemical uses and chemical wastes. Unstable bio‐molecules like enzymes have been stabilized when they get chemically anchored on FSs. The resultant solid bio‐catalysts exhibited very good reusability in many catalytic reactions. Getting provoked from the green chemistry aspects and benefits of FS‐based catalysts, we confer the recent literature and progress focusing on the significance of FSs in heterogeneous catalysis. This review covers the preparative methods, types and catalytic applications of FSs. A special emphasis is given to the metal‐free FS catalysts, multiple FS‐based catalysts and magnetic FSs. Through this review, we presume that the contribution of FSs to green chemistry can be well understood. The future perspective of FSs and the improvements still required for implementing FS‐based catalysts in practical applications have been narrated at the end of this review.

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An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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Substituted pyrans (4H‐Chromenes) are the most significant structural scaffolds in synthetic and medicinal chemistry. They are found in an array of natural products, medicines, and phytochemical compounds, bearing an explicit of pharmacological activities. The structural importance of substituted pyrans has elicited a huge upsurge in the field of synthesis and biology. Different synthetic approaches of 4H‐chromene scaffolds have been discussed systematically to emphasize their significance in the scientific world. The present article summarizes the different synthetic strategies of substituted pyran derivatives via acid‐base catalysis, ionic liquids, nanomaterials, deep eutectic solvents, bio‐based, visible light, metal catalyzed, and so forth developed in the last decade. Moreover, this article will definitely contribute to the scientific world for developing synthetically and biologically important pyran analogs.

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One-pot synthesis of pyran derivatives using silica-coated magnetic nanoparticles functionalized with piperidinium benzene-1,3-disulfonate as a new efficient reusable catalyst

Cited by 9 publications

References 49 publications

Preparation and characterization of hexamethylenetetramine‐functionalized magnetic nanoparticles and their application as novel catalyst for the synthesis of pyranopyrazole derivatives

Preparation and characterization of hexamethylenetetramine‐functionalized magnetic nanoparticles and their application as novel catalyst for the synthesis of pyranopyrazole derivatives

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

An overview of recent advances in the catalytic synthesis of substituted pyrans

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