Investigation of halloysite nanotubes and Schiff base combination with deposited copper iodide nanoparticles as a novel heterogeneous catalytic system

AbstractThe design, preparation and characterization of a novel composite based on functionalization of halloysite nanoclay with Schiff base followed by immobilization of copper iodide as nanoparticles is revealed. This novel nano composite was fully characterized by utilization of FTIR, SEM/EDX, TGA, XRD and BET techniques. This Cu(I) NPs immobilized onto halloysite was successfully examined as a heterogeneous, thus easily recoverable and reusable catalyst in one of classist organic name reaction so-called “Click Reaction”. That comprised a three component reaction of phenylacetylene, α-haloketone or alkyl halide and sodium azide in aqueous media to furnish 1,2,3‐triazoles in short reaction time and high yields. Remarkably, the examination of the reusability of the catalyst confirmed that the catalyst could be reused at least six reaction runs without appreciable loss of its catalytic activity.

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Aqueous Media Preparation of Pyrido[d]pyrimidines Over Calcined TiO2- SiO2 Nanocomposite as an Efficient Catalyst at Ambient Temperature

Letters in Organic Chemistry ◽

10.2174/1570178616666181210102146 ◽

2019 ◽

Vol 16 (11) ◽

pp. 915-921

Author(s):

Nafiseh Yaltaghian-Khiabani ◽

Shahrzad Abdolmohammadi ◽

Sepehr Sadegh-Samiei

Keyword(s):

Ambient Temperature ◽

Titanium Dioxide Nanoparticles ◽

Wide Spectrum ◽

High Surface ◽

Aqueous Media ◽

Reusable Catalyst ◽

Efficient Catalyst ◽

X Ray ◽

Three Component Reaction ◽

High Yields

Pyridopyrimidines represent a highly important class of compounds which exhibit a wide spectrum of biological properties. Nanoscale metal oxide catalysts have been extensively studied for their application in organic reactions owing to their special features such as high surface area and pore sizes as supports. Titanium dioxide nanoparticles (TiO2 NPs) are an attractive candidate for readily available cheap nanocatalysts, due to their unique properties such as being non-toxic, moisture stable and reusable catalyst. 7-amino-2,4-dioxo-5-aryl-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitriles were synthesized through the reaction of 4(6)-aminouracil, aromatic aldehydes, and malononitrile using calcined TiO2-SiO2 nanocomposite as a reusable catalyst in water at ambient temperature. All the synthesized compounds were well characterized by their elemental analyses, IR, 1H and 13C NMR spectroscopy. The synthesized catalyst was fully characterized by the powder X-ray diffraction (XRD), the scanning electron microcopy (SEM), the transmission electron microscopy (TEM), and the x-ray fluorescence (XRF) techniques. The reaction proceeded through calcined TiO2-SiO2 nanocomposite catalyzed three-component reaction affording twelve target compounds in high yields. This method introduced a novel protocol to provide 7-amino-2,4-dioxo-5-aryl-1,2,3,4-tetrahydropyrido[2,3- d]pyrimidine-6-carbonitrile derivatives and offer several advantages like very simple operation, using inexpensive, recyclable and non-toxic catalyst, mild reaction conditions, high yields of products (92- 98%), short reaction times (2.5-4 h), and green aspects by avoiding toxic catalysts and hazardous solvents.

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Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl

Synthesis ◽

10.1055/s-0037-1610755 ◽

2020 ◽

Vol 52 (11) ◽

pp. 1707-1718

Author(s):

Nasser Etivand ◽

Jabbar Khalafy ◽

Mohammad G. Dekamin

Keyword(s):

Aqueous Media ◽

Thiobarbituric Acid ◽

Environmentally Benign ◽

The Novel ◽

One Pot ◽

Synthetic Strategy ◽

Three Component Reaction ◽

High Yields ◽

Green Procedure ◽

Arylglyoxal Monohydrates

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

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Efficient Synthesis 2,3-Dihydroquinazolin-4(1H)-Ones Using Coconut Shell Char Sulfonic Acid as a Reusable Catalyst in Ethanol

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.989-994.83 ◽

2014 ◽

Vol 989-994 ◽

pp. 83-86

Author(s):

Xuan Yan Liu ◽

Zhi Gao Yang

Keyword(s):

Sulfonic Acid ◽

Biginelli Reaction ◽

Acid Catalyst ◽

Coconut Shell ◽

Reusable Catalyst ◽

Efficient Synthesis ◽

One Pot ◽

Efficient Catalyst ◽

Three Component Reaction ◽

High Yields

3,4-Dihydropyrimidin-2(1H)-ones derivatives were synthesized in moderate to high yields in one-pot three component reaction from the corresponding aldehydes, 1,3-dicarbonyl compounds and urea, Coconut shell char sulfonic acid (CSCSA) used as a reusable, and efficient catalyst. Compared to the classical acid catalyst, This new protocol for the Biginelli reaction includes the following important features: excellent yields, non-toxic, inexpensive and easily available reagent.

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A magnetic porous chitosan-based palladium catalyst: a green, highly efficient and reusable catalyst for Mizoroki–Heck reaction in aqueous media

New Journal of Chemistry ◽

10.1039/c5nj01337b ◽

2015 ◽

Vol 39 (10) ◽

pp. 7988-7997 ◽

Cited By ~ 35

Author(s):

Barahman Movassagh ◽

Nasrin Rezaei

Keyword(s):

Heterogeneous Catalyst ◽

Palladium Catalyst ◽

Heck Reaction ◽

Aqueous Media ◽

Reusable Catalyst ◽

Highly Efficient ◽

Highly Active ◽

Porous Chitosan ◽

High Yields ◽

Recyclable Heterogeneous Catalyst

We have prepared a highly active and recyclable heterogeneous catalyst for the Heck reaction in aqueous media in high yields.

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Grinding Synthesis of Pyrazolyl-Bis Coumarinyl Methanes Using Potassium 2-Oxoimidazolidine-1,3-diide

Current Organic Synthesis ◽

10.2174/1570179416666190101142542 ◽

2019 ◽

Vol 16 (2) ◽

pp. 303-308 ◽

Cited By ~ 2

Author(s):

Kazem Hematinezhad ◽

Mohammad Nikpassand ◽

Leila Zare Fekri

Keyword(s):

Reaction Time ◽

Room Temperature ◽

Aqueous Media ◽

13C Nmr Spectroscopy ◽

Reusable Catalyst ◽

Reduced Pressure ◽

Elemental Analyses ◽

Nucleophilic Addition Reaction ◽

High Yields ◽

Work Up

Aim and Objective: Potassium 2-oxoimidazolidine-1,3-diide (POImD) as a novel and reusable catalyst was used for the synthesis of pyrazolyl-bis coumarinyl methanes by a nucleophilic addition reaction of synthetized pyrazolecarbaldehyde and two equivalents of 4-hydroxycoumarin under grinding. The catalyst can be reused and recovered several times without loss of activity. This method provides several advantages such as eco-friendliness, simple work-up and shorter reaction time as well as excellent yields. All of the synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and elemental analyses. Material and Method: Synthetized pyrazole carbaldehyde 1a (1 mmol), 4-hydroxycoumarin 2 (2 mmol), 1 mmol of POImD and 10mL of H2O were ground in a mortar by a pestle for 30-90 minutes. After the completion of the reaction, as monitored by TLC on silica gel using ethyl acetate/n-hexane (1:2), the mixture was allowed to cool to room temperature. After completion of the reaction, we extracted the product with CH2Cl2/H2O. This was followed by separation of phases, evaporation of the organic phase and recrystallization of the residue with 50 mL of ethanol/H2O (1:1). The pure product was then obtained in 87 to 96% yield. The aqueous phase was concentrated under reduced pressure to recover the catalyst for subsequent use. Results: To continue our ongoing studies to synthesize heterocyclic and pharmaceutical compounds by mild, facile and efficient protocols, herein we wish to report our experimental results on the synthesis of pyrazolylbis coumarinyl methanes, using various synthetized pyrazole carbaldehydes and 4-hydroxycoumarin in the presence of POImD in aqueous media at room temperature. Conclusion: Finally, we developed an efficient, fast and convenient procedure for the three-component synthesis of pyrazolyl-bis coumarinyl methanes through the reaction of pyrazole carbaldehydes and 4- hydroxycoumarin, using POImD as a novel and reusable catalyst. The remarkable advantage offered by this method is that the catalyst is non-toxic, inexpensive, easy to handle and reusable. A short reaction time, simple work-up procedure, high yields of product with better purity and the green aspect by avoiding a hazardous solvent and a toxic catalyst are the other advantages. To the best of our knowledge, this is the first report on the synthesis of pyrazolyl-bis coumarinylmethane derivatives using potassium 2-oxoimidazolidine-1,3-diide (POImD).

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Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate

Journal of Chemical Research ◽

10.3184/174751917x14859570937758 ◽

2017 ◽

Vol 41 (3) ◽

pp. 136-138 ◽

Cited By ~ 2

Author(s):

Sabereh Bougan ◽

Alireza Hassanabadi

Keyword(s):

Green Chemistry ◽

Organic Solvent ◽

Green Synthesis ◽

Aqueous Media ◽

Reaction Times ◽

Aromatic Aldehydes ◽

Efficient Synthesis ◽

One Pot ◽

Three Component Reaction ◽

High Yields

A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.

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Cube-octameric silsesquioxane-mediated cargo copper Schiff base for efficient click reaction in aqueous media

Journal of Molecular Catalysis A Chemical ◽

10.1016/j.molcata.2015.12.022 ◽

2016 ◽

Vol 414 ◽

pp. 47-54 ◽

Cited By ~ 47

Author(s):

Ali Akbari ◽

Nasser Arsalani ◽

Mojtaba Amini ◽

Esmaiel Jabbari

Keyword(s):

Schiff Base ◽

Click Reaction ◽

Aqueous Media

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Fe3O4/g-C3N4 Nanocomposites as a Reusable Catalyst for the Synthesis of 5-Arylidenepyrimidine-2,4,6-(1H,3H,5H)-Trione and Pyrano-Pyrimidinone Derivatives in Aqueous Media

Journal of Nanoscience and Nanotechnology ◽

10.1166/jnn.2020.17863 ◽

2020 ◽

Vol 20 (9) ◽

pp. 5433-5444

Author(s):

Farhad Shirini ◽

Fatemeh Kamali

Keyword(s):

Carbon Nitride ◽

Aqueous Media ◽

Reaction Times ◽

Significant Loss ◽

Graphitic Carbon Nitride ◽

Reusable Catalyst ◽

Magnetic Nanocatalyst ◽

Reaction Conditions ◽

Simple Preparation ◽

High Yields

A green magnetic nanocatalyst is developed by immobilization of Fe3O4 on Graphitic carbon nitride (g-C3N4) support for the efficacious synthesis of 5-arylidenepyrimidine-2,4,6-(1H,3H,5H)-trione and pyrano-pyrimidinone derivatives in aqueous media. The most momentous features of the present protocol are the simple preparation of the catalyst, mild reaction conditions, short reaction times and high yields of the products. Moreover, the magnetic nanocatalyst Fe3O4/g-C3N4 can be recycled effectively and reused several times, without a significant loss in reactivity.

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Highly efficient one-pot three-component Betti reaction in water using reverse zinc oxide micelles as a recoverable and reusable catalyst

RSC Advances ◽

10.1039/c6ra28599f ◽

2017 ◽

Vol 7 (23) ◽

pp. 13868-13875 ◽

Cited By ~ 12

Author(s):

Jie Mou ◽

Gan Gao ◽

Chen Chen ◽

Jie Liu ◽

Jian Gao ◽

...

Keyword(s):

Zinc Oxide ◽

Aqueous Media ◽

Reusable Catalyst ◽

Efficient Synthesis ◽

One Pot ◽

Highly Efficient ◽

Three Component Reaction ◽

Reaction In Water

An efficient synthesis of Betti basesviaa one-pot three-component reaction of 2-naphthol, substituted aldehydes and anilines in aqueous media is reported.

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