Using acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate in selective nitration of phenols under mild conditions

2009 ◽  
Vol 6 (1) ◽  
pp. 159-164 ◽  
Author(s):  
H. Tajik ◽  
K. Niknam ◽  
F. Parsa
Keyword(s):  
Ionic Liquid ◽  
Hydrogen Sulfate ◽  
Mild Conditions ◽  
Acidic Ionic Liquid ◽  
Selective Nitration

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.

Efficient pseudo five-component synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives promoted by a novel ionic liquid catalyst

2018 ◽  
Vol 73 (3-4) ◽  
pp. 191-195 ◽  
Author(s):  
Zahra Abshirini ◽  
Abdolkarim Zare
Keyword(s):  
Ionic Liquid ◽  
Disulfonic Acid ◽  
Thermal Gravimetric ◽  
One Pot ◽  
Mild Conditions ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
The One ◽  
C Nmr

AbstractIn this research, initial production and characterization of a novel Brønsted-acidic ionic liquid, namely,N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2), has been described (characterization was achieved using Fourier-transform infrared spectroscopy,1H nuclear magnetic resonance (NMR),13C NMR, and mass and thermal gravimetric spectra). Thereafter, utilization of [TMEDSA][HSO4]2as a highly effectual catalyst for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives through the one-pot pseudo five-component reaction of phenylhydrazine (2 eq.) with ethyl acetoacetate (2 eq.) and arylaldehydes (1 eq.) in relatively mild conditions, has been reported.

Magnetic Nanoparticles Supported Acidic Ionic Liquid as a Highly Active and Reusable Catalyst for Esterification

2016 ◽  
Vol 852 ◽  
pp. 485-488 ◽  
Author(s):  
Qiang Zhang ◽  
Xin Zhao ◽  
Xue Hua Zhu ◽  
Ji Hang Li
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Magnetic Nanoparticles ◽  
Catalytic Performance ◽  
Significant Loss ◽  
Reusable Catalyst ◽  
Hydrogen Sulfate ◽  
External Magnet ◽  
Acidic Ionic Liquid ◽  
Highly Active

A magnetic nanoparticles supported dual acidic ionic liquid catalyst was prepared via anchoring 3-sulfobutyl-1-(3-propyltriethoxysilane) imidazolium hydrogen sulfate onto the surface of silica-coated Fe3O4 nanoparticles. And this novel supported acidic ionic liquid catalyst showed good catalytic performance in esterification. More importantly, the catalyst could be easily recovered by an external magnet and reused six times without significant loss of catalytic activity.

Silica Gel Supported Dual Acidic Ionic Liquid as a Recyclable and Efficient Catalyst for Esterification and Acetalization Reactions

2011 ◽  
Vol 233-235 ◽  
pp. 1336-1339 ◽  
Author(s):  
Qiang Zhang ◽  
Hong Su ◽  
Jun Luo
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Silica Gel ◽  
Covalent Bond ◽  
High Catalytic Activity ◽  
The Novel ◽  
Hydrogen Sulfate ◽  
Efficient Catalyst ◽  
Acidic Ionic Liquid

A supported dual acidic ionic liquid was prepared via anchoring 3-sulfobutyl-1-(3-propyltriethoxysilane) imidazolium hydrogen sulfate onto common silica gel by covalent bond. The novel immobilized acidic ionic liquid illustrated high catalytic activity in esterification and acetalization reactions. The products could be separated by simple decantation and the recovered catalyst could be recycled without remarkable loss of catalytic activity even after eight runs for esterification and six runs for acetalization.

Highly efficient and stereoselective synthesis of (2Z)-2-(halomethyl)alk-2-enoates in acidic ionic liquid

2005 ◽  
Vol 2005 (2) ◽  
pp. 96-98 ◽  
Author(s):  
Taokei Ying ◽  
Weiliang Bao ◽  
Zhonghua Wang ◽  
Yongmin Zhang
Keyword(s):  
Ionic Liquid ◽  
Stereoselective Synthesis ◽  
Hydrogen Sulfate ◽  
Acidic Ionic Liquid ◽  
Highly Efficient ◽  
High Stereoselectivity

NaCl, NaBr and NaI immobilised in 1-butyl-3-methylimidazolinium hydrogen sulfate ([bmim][HSO4]) ionic liquid was found to be an efficient halogenation system for the conversion of Baylis-Hillman adducts, 3-hydroxy-2-methylenealkanoates, into (2Z)-2-(halomethyl)alk-2-enoates. To maintain high stereoselectivity the protocol provides significant improvements over existing procedures.

Synthesis of 2-arylbenzimidazoles under mild conditions catalyzed by a heteropolyacid-containing task-specific ionic liquid and catalyst investigation by electrospray (tandem) mass spectrometry

RSC Advances ◽  
2015 ◽  
Vol 5 (85) ◽  
pp. 69418-69422 ◽  
Author(s):  
Haline G. O. Alvim ◽  
Heibbe C. B. de Oliveira ◽  
Giovana A. Bataglion ◽  
Marcos N. Eberlin ◽  
Luciana M. Ramos ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Ionic Liquid ◽  
Tandem Mass Spectrometry ◽  
Condensation Reaction ◽  
Tandem Mass ◽  
Hydrogen Sulfate ◽  
Electrospray Tandem Mass Spectrometry ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Task Specific Ionic Liquid

A task-specific ionic liquid constituted by a Bronsted acid (1-(3-sulfopropyl)-3-methyl-imidazolium hydrogen sulfate), namely MSI, and by [PW12O40]3−, namely PW, was used for the condensation reaction in the synthesis of 2-arylbenzimidazoles.

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