Highly effectual synthesis of 4,6-diarylpyrimidin-2(1H)-ones using N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate as a dual-functional catalyst

2018 ◽  
Vol 73 (9) ◽  
pp. 635-640 ◽  
Author(s):  
Roghayyeh Khanivar ◽  
Abdolkarim Zare
Keyword(s):  
Ionic Liquid ◽  
Reaction Mechanism ◽  
Catalytic Amount ◽  
Disulfonic Acid ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Dual Functional ◽  
Solvent Free Conditions ◽  
The One ◽  
Reaction Media

AbstractThe highly effectual synthesis of 4,6-diarylpyrimidin-2(1H)-ones via the one-pot multicomponent reaction of acetophenones with arylaldehydes and urea in the presence of trimethylsilyl chloride and a catalytic amount of the ionic liquid N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2) under solvent-free conditions has been described. The reaction results and conditions of the catalytic system have been compared with previously reported catalysts. [TMEDSA][HSO4]2 afforded better results in comparison with the reported catalysts in terms of one or more of these factors: yield, temperature, the reaction media, time, and generality. Moreover, a plausible reaction mechanism based on dual functionality of the catalyst has been proposed.

1,3-Disulfonic acid imidazolium hydrogen sulfate: a reusable and efficient ionic liquid for the one-pot multi-component synthesis of pyrimido[4,5-b]quinoline derivatives

RSC Advances ◽  
2015 ◽  
Vol 5 (30) ◽  
pp. 23586-23590 ◽  
Author(s):  
Kamal Mohammadi ◽  
Farhad Shirini ◽  
Asieh Yahyazadeh
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Disulfonic Acid ◽  
Quinoline Derivatives ◽  
Hydrogen Sulfate ◽  
Efficient Synthesis ◽  
One Pot ◽  
The One

1,3-Disulfonic acid imidazolium hydrogen sulfate (DSIMHS) has been used for the simple and efficient synthesis of pyrimido[4,5-b]quinoline derivatives. The procedure gave the products in excellent yields in very short reaction times.

Design of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as a dual-catalyst for the one-pot multi-component synthesis of 1,2,4,5-tetrasubstituted imidazoles

2013 ◽  
Vol 19 (3) ◽  
pp. 721-726 ◽  
Author(s):  
Mohammad Ali Zolfigol ◽  
Ardeshir Khazaei ◽  
Ahmad Reza Moosavi-Zare ◽  
Abdolkarim Zare ◽  
Zhila Asgari ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Disulfonic Acid ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
The One ◽  
Tetrasubstituted Imidazoles

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.

Glutamic Acid as an Efficient and Green Catalyst for the One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles under Thermal, Solvent-Free Conditions

2017 ◽  
Vol 41 (11) ◽  
pp. 673-675 ◽  
Author(s):  
Fahimeh Khazaee Feizabad ◽  
Khatereh Khandan-Barani ◽  
Alireza Hassanabadi
Keyword(s):  
Glutamic Acid ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Solvent Free ◽  
One Pot ◽  
Green Catalyst ◽  
Aryl Aldehydes ◽  
Solvent Free Conditions ◽  
The One ◽  
Tetrasubstituted Imidazoles

A high-yielding synthesis of 1,2,4,5-tetrasubstituted imidazoles is described, involving the reaction of 1,2-dicarbonyl compounds, aryl aldehydes, amines and ammonium acetate in the presence of a catalytic amount of glutamic acid under thermal, solvent-free conditions. The salient features of this protocol are aerobic conditions, a non-hazardous green catalyst, short reaction times and mild reaction conditions.

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