Morpholinium hydrogen sulfate (MHS) ionic liquid as an efficient catalyst for the synthesis of bio-active multi-substituted imidazoles (MSI) under solvent-free conditions

2017 ◽  
Vol 72 (1) ◽  
pp. 23-33 ◽  
Author(s):  
Adel A. Marzouk ◽  
Antar A. Abdelhamid ◽  
Shaaban K. Mohamed ◽  
Jim Simpson
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Biologically Active ◽  
High Yield ◽  
Hydrogen Sulfate ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Very High

AbstractMorpholinium hydrogen sulfate as an ionic liquid was employed as a catalyst for the synthesis of a biologically active series of multi-substituted imidazoles by a four-component reaction involving the combination of benzil with different aromatic aldehydes, ammonium acetate, and 1-amino-2-propanol under solvent-free conditions. The key advantages of this method are shorter reaction times, very high yield, and ease of processing. Furthermore, the resulting products can be purified by a non-chromatographic method and the ionic liquid catalyst is reusable. All of these novel compounds have been fully characterized from spectral data. The X-ray crystal structures of two representative molecules are also detailed.

Preparation and Characterization of a Novel Room Temperature Dicationic Ionic Liquid and its Application in the Synthesis of Xanthenediones Under Solvent-Free Conditions

2018 ◽  
Vol 21 (8) ◽  
pp. 602-608 ◽  
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Reaction Times ◽  
Significant Loss ◽  
Solvent Free ◽  
Acidity Function ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Hammett Acidity Function ◽  
Dicationic Ionic Liquid

Aim and Objective: In the present work, 1, 1’-sulfinyldiethylammonium bis (hydrogen sulfate) as a novel room temperature dicationic ionic liquid was synthesized and used as a catalyst for xanthenediones synthesis. Material and Method: The dicationic ionic liquid has been synthesized using ethylamine and thionyl chloride as precursors. Then, by the reaction of [(EtNH2)2SO]Cl2 with H2SO4, [(EtNH2)2SO][HSO4]2 was prepared and after that, it was characterized by FT-IR, 1H NMR, 13C NMR as well as Hammett acidity function. This dicationic ionic liquid was used as a catalyst for the synthesis of xanthenediones via condensation of structurally diverse aldehydes and dimedone under solvent-free conditions. The progress of the reaction was monitored by thin layer chromatography (ethyl acetate/n-hexane = 3/7). Results: An efficient solvent-free method for the synthesis of xanthenediones has been developed in the presence of [(EtNH2)2SO][HSO4]2 as a powerful catalyst with high to excellent yields, and short reaction times. Additionally, recycling studies have demonstrated that the dicationic ionic liquid can be readily recovered and reused at least four times without significant loss of its catalytic activity. Conclusion: This new dicationic ionic liquid can act as a highly efficient catalyst for xanthenediones synthesis under solvent-free conditions.

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

scholarly journals K2CO3: A Mild and Efficient Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems by Grinding Method Under Solvent-Free Conditions

2017 ◽  
Vol 25 (2) ◽  
pp. 163-178 ◽  
Author(s):  
Reza Heydari ◽  
Rohollah Rahimi ◽  
Mehrnoosh Kangani ◽  
Afshin Yazdani-Elah-Abadi ◽  
Mojtaba Lashkari
Keyword(s):  
Room Temperature ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Synthetic Methods ◽  
One Pot ◽  
Efficient Catalyst ◽  
Grinding Method ◽  
Solvent Free Conditions ◽  
The One

Abstract The potassium carbonate was applied as a green and efficient catalyst for the one-pot synthesis of pyran annulated heterocyclic systems, via the condensation between aromatic aldehydes, malononitrile and dimedone/1-naphtole by a grinding method at room temperature and solvent-free conditions. Short reaction times, environmentally friendly procedure and excellent yields are the main advantages of this procedure which makes it more economic than other environmentally synthetic methods.

scholarly journals Mg(HSO4)2/SiO2 as a Highly Efficient Catalyst for the Green Preparation of 2-Aryl-1,3-Dioxalanes/Dioxanes and Linear Acetals

2012 ◽  
Vol 2012 ◽  
pp. 1-5 ◽  
Author(s):  
Fariba Jafari ◽  
Saeed Khodabakhshi
Keyword(s):  
Organic Solvents ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
High Yield ◽  
Hydrogen Sulfate ◽  
Green Process ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Work Up ◽  
Environmentally Friendly Method

Silica-supported magnesium hydrogen sulfate has been used as a recyclable catalyst for the synthesis of some linear and cyclic aromatic acetals under solvent-free conditions. This environmentally friendly method has advantages, such as high yield of products, simple work-up procedure, and avoidance of the organic solvents, which will contribute in serving as a green process greatly.

Chlorosulfonic Acid Supported Piperidine-4-carboxylic Acid (PPCA) Functionalized Fe3O4 Nanoparticles (Fe3O4-PPCA): The Efficient, Green and Reusable Nanocatalyst for the Synthesis of Pyrazolyl Coumarin Derivatives under Solvent-Free Conditions

2019 ◽  
Vol 22 (2) ◽  
pp. 123-128
Author(s):  
Setareh Habibzadeh ◽  
Hassan Ghasemnejad-Bosra ◽  
Mina Haghdadi ◽  
Soheila Heydari-Parastar
Keyword(s):  
Carboxylic Acid ◽  
Fe3o4 Nanoparticles ◽  
High Efficiency ◽  
Reaction Times ◽  
Chlorosulfonic Acid ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Magnetic Nanocatalyst ◽  
One Pot ◽  
Solvent Free Conditions

Background: In this study, we developed a convenient methodology for the synthesis of coumarin linked to pyrazolines and pyrano [2,3-h] coumarins linked to 3-(1,5-diphenyl-4,5- dihydro-1H-pyrazol-3-yl)-chromen-2-one derivatives using Chlorosulfonic acid supported Piperidine-4-carboxylic acid (PPCA) functionalized Fe3O4 nanoparticles (Fe3O4-PPCA) catalyst. Materials and Methods:: Fe3O4-PPCA was investigated as an efficient and magnetically recoverable Nanocatalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with a variety of aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be easily recovered by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. Results and Conclusion: The advantages of this protocol are the use of commercially available materials, simple and an inexpensive procedure, easy separation, and an eco-friendly procedure, and it shows good reaction times, good to high yields, inexpensive and practicability procedure, and high efficiency.

scholarly journals Immobilization of Lewis acidic ionic liquid on perlite nanoparticle surfaces as a highly efficient solid acid catalyst for the solvent-free synthesis of xanthene derivatives

RSC Advances ◽  
2019 ◽  
Vol 9 (35) ◽  
pp. 19940-19948 ◽  
Author(s):  
L. Moradi ◽  
M. Mirzaei
Keyword(s):  
Ionic Liquid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Solvent Free ◽  
High Yield ◽  
Efficient Catalyst ◽  
Acidic Ionic Liquid ◽  
Highly Efficient ◽  
Xanthene Derivatives ◽  
Lewis Acidic Ionic Liquid

Perlite nanoparticles were prepared, modified with Lewis acidic ionic liquid, and used as a highly efficient catalyst for the eco-friendly, solvent free and high yield synthesis of xanthenesviaa multicomponent reaction.

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