Nano-NiZr4(PO4)6 as a superior catalyst for the synthesis of propargylamines under ultrasound irradiation

2018 ◽  
Vol 73 (3-4) ◽  
pp. 185-189 ◽  
Author(s):  
Hossein Shahbazi-Alavi ◽  
Seyed Hadi Nazemzadeh ◽  
Abolfazl Ziarati ◽  
Javad Safaei-Ghomi
Keyword(s):  
Rapid Method ◽  
Aromatic Aldehydes ◽  
Ultrasound Irradiation ◽  
Catalyst Loading ◽  
Atom Economy ◽  
Three Component Reaction ◽  
Wide Range ◽  
Low Catalyst Loading ◽  
Short Times

AbstractAn easy and rapid method for the synthesis of propargylamines has been achieved through a three-component reaction of phenylacetylene, aromatic aldehydes, and morpholine or piperidine using nano-NiZr4(PO4)6under ultrasound irradiation. Atom economy, a wide range of products, excellent yields in short times, reusability of the catalyst, and low catalyst loading are some of the important features of this protocol.

Three-Component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the presence of potassium 2,5-dioxoimidazolidin-1-ide

2021 ◽  
Vol 25 ◽  
Author(s):  
Neda Reihani ◽  
Hamzeh Kiyani
Keyword(s):  
Ethylene Glycol ◽  
Ethyl Acetoacetate ◽  
Reaction Medium ◽  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Efficient Synthesis ◽  
Current Process ◽  
High Yields ◽  
Low Catalyst Loading

: An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate of this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used for the synthesize of the number of substituted isoxazole-5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over the some reported catalysts.

scholarly journals Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives

2019 ◽  
Vol 10 (2) ◽  
pp. 166-170 ◽  
Author(s):  
Fatma Ahmed Abo Elsoud ◽  
Mohamed Abd-Elmonem ◽  
Mohamed Abo Elsebaa ◽  
Kamal Usef Sadek
Keyword(s):  
Kojic Acid ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Short Reaction Time ◽  
Biologically Relevant ◽  
Three Component Reaction ◽  
High Yields ◽  
Organometallic Catalyst ◽  
Work Up

Efficient synthesis of non-annulated 2-amino-4H-pyrans and 2-amino-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives, which are biologically relevant heterocycles is achieved, utilizing a domino three-component reaction of ethyl acetoacetate or kojic acid with aromatic aldehydes and malononitrile catalyzed by Zn(L-proline)2 as reusable organometallic catalyst. The process exhibits high atom economy, short reaction time, simple work up, high yields and environmentally friendly nature. Excellent yields of the targeted molecules have been obtained.

scholarly journals Ferrocene-Containing Ionic Liquid Supported on Silica Nanospheres (SiO2@Imid-Cl@Fc) as a Mild and Efficient Heterogeneous Catalyst for the Synthesis of Pyrano[3,2-b]Pyran Derivatives Under Ultrasound Irradiation

2018 ◽  
Vol 42 (1) ◽  
pp. 7-12 ◽  
Author(s):  
Reza Teimuri-Mofrad ◽  
Somayeh Esmati ◽  
Masoumeh Rabiei ◽  
Mahdi Gholamhosseini-Nazari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Ultrasound Irradiation ◽  
Xrd Analysis ◽  
Catalytic Performance ◽  
Significant Loss ◽  
One Pot ◽  
X Ray ◽  
Three Component Reaction

A novel heterogeneous silica nanosphere-supported ferrocene-containing ionic liquid catalyst (SiO2@Imid-Cl@Fc) was designed and synthesised and was systematically characterised by Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) and X-ray diffraction (XRD) analysis. The catalytic activity of the SiO2@Imid-Cl@Fc catalyst was tested in a one-pot, three-component reaction of malononitrile and kojic acid with 15 aromatic aldehydes at room temperature under ultrasound irradiation. The products were pyrano[3,2-b]pyran derivatives, four of which are new. The catalyst exhibited good catalytic performance over short reaction times (15–20 min) and could be recycled at least five times without significant loss of activity.

scholarly journals Natural dolomitic limestone catalyzed synthesis of benzimidazoles, dihydropyrimidinones and highly substituted pyridines under ultrasound irradiation

2020 ◽  
Author(s):  
Kumar Godugu ◽  
Venkata Divya Sri Yadala ◽  
Mohammad Khaja Mohinuddin Pinjari ◽  
Thrivikram Reddy Gundala ◽  
Lakshmi Reddy Sanapareddy ◽  
...  
Keyword(s):  
Ultrasound Irradiation ◽  
Significant Loss ◽  
Catalyst Loading ◽  
Dolomitic Limestone ◽  
X Ray Diffraction ◽  
Rapid Construction ◽  
Substituted Pyridines ◽  
Ft Ir ◽  
Low Catalyst Loading ◽  
First Time

In this paper, for the first time, naturally occurring dolomitic limestone is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable N-heterocycles, 2-aryl-1-arylmethyl-1H-benzo[d]imidazoles, dihydropyrimidinones/ thiones and 2-amino-4-aryl-3,5-dicarbonitrile-6-sulfanyl-pyridines in good to excellent isolated yields via a rapid construction of C-N, C-C and C-S bond formations in 1:1 ratio of ethanol:H2O under ultrasound irradiation. Dolomitic limestone is characterized by X-ray diffraction (XRD), FT-IR, Raman and SEM with EDAX analyses. Further, the catalyst is environmentally benevolent, non-toxic, most abundant, easy to handle low catalyst loading and is reused 7 times without significant loss of catalytic activity. Hence, the catalyst is greener alternative for the synthesis of aforementioned N-heterocycles as compared with the existing reported catalysts.

scholarly journals Synthesis and Catalytic Applications of Ultrasmall Copper Nanoparticles Using Aloe Vera Plant Extract

2020 ◽  
Author(s):  
Rajagopal Ramkumar ◽  
Shradha Sapru ◽  
Panthalattu Parambil Archana
Keyword(s):  
Catalytic Activity ◽  
Copper Nanoparticles ◽  
Plant Extract ◽  
Aloe Vera ◽  
Catalyst Loading ◽  
Water Medium ◽  
Reaction Conditions ◽  
Three Component Reaction ◽  
Catalytic Applications ◽  
Low Catalyst Loading

<div>An extract of <i>Aloe Vera</i> acts as a powerful reducing agent for the synthesis of ultrasmall copper nanoparticles (CuNPs) in water medium. The prepared copper nanoparticles are characterized by XRD, HRTEM and UV-Vis analysis. The diameter of the prepared nanoparticle is less than 5 nm. The catalytic activity of CuNPs has been successfully evaluated for the three-component reaction to synthesize 1,2,3-triazoles and chalcone tethered 1,2,3-triazoles with low catalyst loading and under mild reaction conditions. These triazoles are further utilized for the synthesis of dihydropyrazines.</div>

The Discovery of Ultrasound Irradiation as a Useful Tool for Accelerating Petasis Three-component Reaction: Synthesis of α-Arylglycines

2018 ◽  
Vol 15 (2) ◽  
pp. 256-266 ◽  
Author(s):  
Fan Yun ◽  
Chunhui Cheng ◽  
Jingxuan Li ◽  
Pingwah Tang ◽  
Qipeng Yuan
Keyword(s):  
Reaction Time ◽  
Glyoxylic Acid ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Secondary Amines ◽  
One Pot ◽  
Petasis Reaction ◽  
Three Component Reaction ◽  
Wide Range ◽  
High Yields

Aim and Objective: α-Arylglycines belong to an important class of non-proteinogenic amino acids. Petasis 3-component, one-pot reaction lends itself to be suitable for the synthesis of α-Arylglycines. Because of the low reactivity, Petasis reaction requires long reaction time. Our objective is to use ultrasound irradiation to accelerate this versatile Petasis' synthesis of α-Arylglycines. Materials and Methods: Ultrasound irradiation as a physical tool to accelerate the Petasis 3-component reaction without any auxiliary catalyst can significantly shorten the reaction time. The operation is simple. It can be applied to a wide range of substrates. In order to highlight the remarkable utility of the ultrasound in Petasis reaction, we have compared side-by-side the reactivity between the reaction with ultrasound and the one without ultrasound. Results: Using ultrasound, the reaction times of Petasis reactions with various amine substrates including primary and secondary amines, heterocyclic amines, with a wide variety of boronic acids having different substituents (activating and deactivating groups) in the phenyl rings, and with glyoxylic acid and salicylic aldehyde were shortened from 5 to more than 20-fold. Conclusion: We have discovered the first examples of an efficient ultrasound-promoted approach for Petasis reaction to prepare a series of α-arylglycines in high yields and in excellent purities. The low reactivity of the reactions in this study were significantly enhanced by the ultrasound irradiation. By virtue of the acceleration and the operational simplicity, the present ultrasound assisted Petasis reaction can find applications in the synthetic areas of the already widely used Petasis three-component reaction.

Chiral α-substituted allylboronates in a one-pot three-component asymmetric allylic alkylation/carbonyl allylation reaction sequence — Applications to the syntheses of (+)-(3R,5R)-3-hydroxy-5-decanolide and (–)-massoialactone

2009 ◽  
Vol 87 (5) ◽  
pp. 650-661 ◽  
Author(s):  
Lisa Carosi ◽  
Dennis G. Hall
Keyword(s):  
Alkyl Substituent ◽  
Catalyst Loading ◽  
Allylic Alkylation ◽  
One Pot ◽  
Sequential Reaction ◽  
Three Component Reaction ◽  
Carbonyl Allylation ◽  
The One ◽  
Low Catalyst Loading ◽  
Very High

The use of different organomagnesium reagents in the copper-catalyzed allylic alkylation of 3-chloropropenyl boronates with chiral phosphoramidite ligands produces the desired α-substituted allylic boronate reagents in high regioselectivity and with modest to high enantioselectivities (up to 96% ee). The size of the incoming alkyl substituent from the organomagnesium reagent was found to impact the yield and selectivity of the allylic alkylation. A one-pot procedure for the preparation of these chiral allylic boronates followed by a Lewis acid (BF3) catalyzed addition to aldehydes delivers the desired allylboration products, homoallylic secondary alcohols, in good yields and very high diastereoselectivity. This three-component reaction methodology was applied to the syntheses of two lactone-containing natural products, (–)-massoialactone and (+)-(3R,5R)-3-hydroxy-5-decanolide. The key step of these syntheses involved the one-pot enantioselective copper-catalyzed allylic alkylation/allylboration reaction with a benzylic aldehyde, and afforded the desired product in 87% yield, 92% ee, and high E/Z selectivity in a ratio of 22:1. Remarkably, the allylic alkylation step of this sequential reaction was performed with a low catalyst loading of 2 mol% on a scale of >15 mmol that can provide multiple grams of the three-component product.

Chitosan-attached nano-Fe3O4 as a superior and retrievable heterogeneous catalyst for the synthesis of benzopyranophenazines using chitosan-attached nano-Fe3O4

2019 ◽  
Vol 74 (10) ◽  
pp. 733-738
Author(s):  
Javad Safaei-Ghomi ◽  
Maryam Tavazo ◽  
Hossein Shahbazi-Alavi
Keyword(s):  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
Catalyst Loading ◽  
High Catalytic Activity ◽  
One Pot ◽  
X Ray ◽  
Wide Range ◽  
Nano Fe3o4 ◽  
Low Catalyst Loading

AbstractA simple and rapid method for the preparation of benzopyranophenazines is presented, involving a one-pot four-component reaction of hydroxynaphthoquinone, o-phenylenediamine, benzaldehydes, and malononitrile with nano-Fe3O4@chitosan as an efficient heterogeneous solid acid catalyst under reflux conditions in ethanol. The catalyst is characterized by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), magnetic susceptibility measurements, energy-dispersive X-ray spectroscopy (EDS), and Fourier transform infrared (FT-IR) spectroscopy. Atom economy, high catalytic activity, a wide range of products, excellent yields in short reaction times, and low catalyst loading are some of the important features of this method.

scholarly journals Synthesis of pyrimidines by Fe3O4@SiO2-L-proline nanoparticles

2020 ◽  
Vol 43 (1) ◽  
pp. 117-124
Author(s):  
Javad Safaei-Ghomi ◽  
Zahra Samadi
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Gravimetric Analysis ◽  
X Ray Diffraction ◽  
X Ray ◽  
Ft Ir ◽  
High Yields ◽  
Low Catalyst Loading ◽  
Ft Ir Spectroscopy

AbstractFe3O4@SiO2-L-proline nanoparticles have been used as an effective catalyst for the preparation of pyrimidines by three-component reactions of 1,3-dimethylbarbituric acid, aromatic aldehydes and 4-methyl aniline or 4-methoxy aniline under reflux condition in ethanol. Fe3O4@SiO2-L-proline nanoparticles have been characterized by scanning electronic microscopy (SEM), powder X-ray diffraction (XRD), vibrating sample magnetometer (VSM), thermal gravimetric analysis (TGA), energy dispersive X-ray (EDS), dynamic light scattering (DLS) and FT-IR spectroscopy. This method provides several advantages including, the reusability of the catalyst, low catalyst loading, atom economy, short reaction times and high yields of products.

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