Sodium alginate: Biopolymeric catalyst for the synthesis of 2-amino-4-arylthiazole derivatives in aqueous medium

Gorji, Samareh; Ghorbani‐Vaghei, Ramin; Alavinia, Sedigheh

doi:10.1016/j.molstruc.2021.129900

Cited by 9 publications

(3 citation statements)

References 49 publications

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“…The structural analysis of the sodium alginate (SA) shows that is formed by a linear copolymer of two homopolymeric blocks of (1→4)-linked α-L-guluronic acid (G) and β-D-mannuronic acid (M) monomers and heteropolymorphic fractions GM, see Scheme 1 [ 30 , 31 ]. All these monomers contain a carboxylate and two hydroxyl groups which can act as a bifunctional heterogeneous organocatalyst for the electrophilic and nucleophilic reactions assisted by carboxylate groups and/or hydrogen bonding [ 32 , 33 , 34 , 35 ]. To get more light on the surface and chemical structural properties, the obtained natural-occurring sodium alginate (SA) was examined by SEM, EDX, FTIR, and NMR analyses.…”

Section: Resultsmentioning

confidence: 99%

Mechanistic Insights into the Selective Synthesis of 4H-Pyran Derivatives On-Water Using Naturally Occurring Alginate from Sargassum muticum: Experimental and DFT Study

Oudghiri

Belattmania

Elmouli

et al. 2022

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The naturally occurring sodium alginate (SA) biopolymer from the Sargassum muticum (Yendo) Fensholt was employed as a green organocatalyst for the synthesis of 4H-pyran derivatives. The naturally extracted macromolecule was fully characterized using different analyses, including nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and Energy Dispersive X-ray Analysis (EDX). The catalytic activity of SA was investigated in the one-pot reaction between aldehydes, malononitrile, and 1,3-dicarbonyl compounds in water at room temperature, and the corresponding 2-amino-3-cyano-4H-pyran derivatives were obtained with good to excellent yields. This organocatalyst was easily separated from the reaction mixture and reused for at least two consecutive cycles without a significant loss of its catalytic activity or selectivity. From the mechanistic point of view, density functional theory (DFT) and NCI analyses were performed for the first time to explain the regioselectivity outcomes for the synthesis of 2-amino-3-cyano-4H-pyran derivatives using SA as a green organocatalyst.

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Section: Resultsmentioning

confidence: 99%

Mechanistic Insights into the Selective Synthesis of 4H-Pyran Derivatives On-Water Using Naturally Occurring Alginate from Sargassum muticum: Experimental and DFT Study

Oudghiri

Belattmania

Elmouli

et al. 2022

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“…1,2 Thiazoles, a class of heterocyclic compounds, have garnered signicant attention due to their ubiquitous presence in the structural composition of various pharmaceuticals (Scheme 1). [3][4][5] Their synthesis, encompassing diverse methodologies such as coupling, cyclization, redox cyclization, oxidative processes, and condensation, underscores their versatility and importance in medicinal chemistry. 6 One standard method for preparing benzothiazole derivatives is the condensation reaction of 2-aminothiophenol with carbonylbearing compounds, particularly aromatic/aliphatic aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of benzothiazoles using an iron-anchored polysulfonamide modified layered double oxide/sodium alginate nanocomposite

Ghiai,

Alavinia,

Ghorbani-Vaghei

et al. 2024

J. Mater. Chem. A

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“…[32] Sodium alginate and F127 surfactant are typical templates for the formation of porous materials by the soft template method. [33,34] For example, Abou Oualid et al used sodium alginate as a template to successfully synthesize mesoporous Ag/ZnO nano hybrid materials by a simple green route. [35] Chu et al and Guan et al used F127 as a template to successfully synthesize composite HZSM-5@cubic ordered mesoporous SiO 2 and mesoporous Al-SBA-16 materials, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐ethoxymethylfurfural from glucose catalyzed by porous tetra‐component metal oxides solid acid

Zhang

Sun

et al. 2022

Can J Chem Eng

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The production of 5-ethoxymethylfurfural (EMF) from cheap and abundant glucose feedstock has attracted a great deal of attention because of its potential applications. Herein, three porous tetra-component metal oxide solid acid catalysts (SO 4 2À /ZFSA-A, SO 4 2À /ZFSA-F-10, SO 4 2À /ZFSA-F-20)containing both Brønsted and Lewis acid sites have been successfully synthesized and can efficiently catalyze the synthesis of EMF from glucose.Particularly, the SO 4 2À /ZFSA-A, SO 4 2À /ZFSA-F-10, and SO 4 2À /ZFSA-F-20 catalysts were prepared under the template of sodium alginate, 10% F127, and 20% F127, respectively. The prepared catalysts were characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), N 2 -adsorption-desorption isotherm, X-ray photoelectron spectroscopy (XPS), thermogravimetry (TG), temperature-programmed desorption of ammonia (NH 3 -TPD), and pyridine infrared spectra (Py-FTIR). The characterization results indicated that all three catalysts have a porous structure. The pore distribution of the SO 4 2À /ZFSA-A catalyst is mainly macroporous and mesoporous, while the SO 4 2À /ZFSA-F-10 and SO 4 2À /ZFSA-F-20 catalysts are mainly mesoporous. The SO 4 2À /ZFSA-F-20 catalyst exhibited the highest catalytic performance due to its large specific surface area, desirable mesoporous structure, high total acidity (especially strong and super strong acidity), and appropriate Lewis/Brønsted acid ratio. By applying SO 4 2À / ZFSA-F-20, the formation of EMF from glucose was successfully catalyzed and EMF was obtained at a yield of 34.56% after 12 h at 160 C. This yield is much higher compared with most other results achieved by solid acids catalysis. In addition, the reaction parameters such as reaction temperature, reaction time, glucose amount, and catalyst dosage were shown to have a significant effect on the catalytic performance. Notably, the SO 4 2À /ZFSA-F-20 catalyst exhibited good reusability, as its activity did not significantly diminish after four rounds of repeated experiments and was successfully reactivated after calcination.

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Sodium alginate: Biopolymeric catalyst for the synthesis of 2-amino-4-arylthiazole derivatives in aqueous medium

Cited by 9 publications

References 49 publications

Mechanistic Insights into the Selective Synthesis of 4H-Pyran Derivatives On-Water Using Naturally Occurring Alginate from Sargassum muticum: Experimental and DFT Study

Mechanistic Insights into the Selective Synthesis of 4H-Pyran Derivatives On-Water Using Naturally Occurring Alginate from Sargassum muticum: Experimental and DFT Study

Synthesis of benzothiazoles using an iron-anchored polysulfonamide modified layered double oxide/sodium alginate nanocomposite

Synthesis of 5‐ethoxymethylfurfural from glucose catalyzed by porous tetra‐component metal oxides solid acid

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