The efficient synthesis of carbon–carbon double bonds via Knoevenagel condensation using red mud packed in a column

Khezri, S. Hadi; Mohammad-Vali, M.; Eftekhari‐Sis, Bagher; Hashemi, Mohammed M.; Baniasadi, M.H.

doi:10.1080/17518250701787830

Cited by 4 publications

(1 citation statement)

References 33 publications

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“…Different natural materials are used as solid support as well as catalysts in a large number of reactions promoting the formation of final products. Natural materials such as different plant parts such as fruits, root extracts [26][27][28][29][30][31][32], clays [33,34], zeolites [35,36] and enzymes [37,38] are used effectively in numerous chemical transformations.…”

Section: Introductionmentioning

confidence: 99%

Synergistic effect of natural chickpea leaf exudates acids in heterocyclization: a greener protocol for benzopyran synthesis

Mali¹,

Shinde²,

Damte³

et al. 2018

R. Soc. open sci.

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Without using any toxic or hazardous reagent, ligand, acid, transition metal catalyst, additives/promoters and organic solvent, green Knoevenagel condensation and tandem Knoevenagel–Michael reactions have been successfully carried out by using chickpea leaf exudates as a naturally sourced Bronsted acid type bio-catalyst. The reaction proceeds in neat chickpea leaf exudates at room temperature in aqueous conditions in very short reaction times, and therefore, it is an evergreen and environmentally sound alternative to the existing protocols for benzopyran synthesis. In comparison to the conventional methods, this synthetic pathway complies with several key requirements of green chemistry principles such as the utilization of biodegradable catalyst obtained from renewable feedstock, auxiliary aqueous conditions, along with waste prevention. The same protocol was also extended to the synthesis of 2H-xanthene-1,8-diones by condensation of aromatic aldehydes with dimedone achieving excellent yields. Thus, the reported protocol offers an attractive option because of its ecological safety, environmental acceptance, sustainability, low-cost straightforward work-up procedure and with excellent values of green chemistry metrics as compared with other reported methods.

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Section: Introductionmentioning

confidence: 99%

Synergistic effect of natural chickpea leaf exudates acids in heterocyclization: a greener protocol for benzopyran synthesis

Mali¹,

Shinde²,

Damte³

et al. 2018

R. Soc. open sci.

View full text Add to dashboard Cite

show abstract

Condensation of Active Methylene and Substituted Aldehydes over Mesoporous Nickel Oxides Nanostructures: A Combined Experimental and DFT Study

2021

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Mesoporous NiO nanoarchitectures (NAs) with controlled hexagonal platelet-and flower-like morphology were synthesized using facile hydrothermal methods in different reaction conditions. The NiO NAs were characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), N 2 adsorption /desorption isotherms, and wide-angle Xray diffraction. It was found that controlled morphology, large surface areas, and high crystallinity of NiO NAs offered high catalytic reactivity toward Knoevenagel condensation reactions. Large reaction yields in an aqueous media and easy separation of the NiO NAs without losing the catalytic activity were observed. Further, the formation mechanism of À C ¼ CÀ bonds over NiO NAs surface was explored by density functional theory (DFT). These findings open a new avenue for efficient À C ¼ CÀ bonds formation using reusable NiO NAs catalyst without using any expensive solvents.

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A Microwave Accelerated Sustainable Approach for the Synthesis of 2-amino-4H-chromenes Catalysed by WEPPA: A Green Strategy

Kamanna

2019

CMIC

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Background: The agricultural wastes as a source offer an excellent alternative to replace many toxic and environmentally hazardous catalysts, due to their least toxicity, ease of biodegradability, and ability to act as a greener catalytic medium. Some of the agro-waste based catalysts reported are BFE, WERSA, WEB, and WEPBA. 2-Amino-4H-chromene derivatives are promising biologically potent heterocyclic compounds, due to their medicinal applications such as antimicrobial, anti-inflammatory, antibacterial, antiviral, anticancer, antidiuretic, anticoagulant and antianaphylactic activities. The present work describes a microwave accelerated, efficient, eco-friendly and economical approach for the synthesis of 2-amino-4H-chromenes through condensation of substituted arylaldehyde, malononitrile and resorcinol/naphthol catalyzed water extract of pomegranate peel ash (WEPPA) under microwave irradiation. The reaction completed within 3-6 min with good to excellent yield of product isolation. The final product isolated by simple filtration and recrystallization gave a spectroscopically pure form of product and did not require further purification. Methods: The pomegranate peel ash water extract as an agro-waste derived catalyst was employed under microwave irradiation for the economical synthesis of 2-amino-4H-chromene derivatives. Results: The reported agro-waste based catalyst was obtained in the absence of external base, additives and solvent-free synthesis of 2-amino-4H-chromene using aryl aldehyde, malononitrile and resorcinol/ naphthol under microwave irradiation. WEPPA acts as a solvent media and catalyst, as it plays a dual role in the synthesis of 2-amino-4H-chromenes. Conclusion: We established an efficient, simple, agro-waste based catalytic approach for the synthesis of 2-amino-4H-chromene derivatives from the condensation of arylaldehyde, malononitrile and resorcinol/α-naphthol/β-naphthol employing WEPPA as an efficient catalyst under microwave synthesis. The method has found to be a greener, economic and eco-friendly approach for the synthesis of chromene scaffolds. The advantages of the present approach are solvent-free, no external metal, chemical base free, short reaction time and isolated product in good to excellent yields. The catalyst is agro-waste derived, which has abundant natural sources available, thus making the present approach a greener one.

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The efficient synthesis of carbon–carbon double bonds via Knoevenagel condensation using red mud packed in a column

Cited by 4 publications

References 33 publications

Synergistic effect of natural chickpea leaf exudates acids in heterocyclization: a greener protocol for benzopyran synthesis

Synergistic effect of natural chickpea leaf exudates acids in heterocyclization: a greener protocol for benzopyran synthesis

Condensation of Active Methylene and Substituted Aldehydes over Mesoporous Nickel Oxides Nanostructures: A Combined Experimental and DFT Study

A Microwave Accelerated Sustainable Approach for the Synthesis of 2-amino-4H-chromenes Catalysed by WEPPA: A Green Strategy

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