1,1′-Sulfinyldipyridinium bis (hydrogen sulfate) ionic liquid: synthesis and application in the temperature-influenced synthesis of novel pyranopyrimidinediones and pyranopyrimidinetriones

RSC Advances ◽  
2014 ◽  
Vol 4 (92) ◽  
pp. 50449-50455 ◽  
Author(s):  
Jayavant D. Patil ◽  
Suyog N. Korade ◽  
Dattaprasad M. Pore
Keyword(s):  
Ionic Liquid ◽  
Hydrogen Sulfate ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid

A novel and robust dication Brønsted acidic ionic liquid as a catalyst for the temperature influenced synthesis of novel pyranopyrimidinediones and pyranopyrimidinetriones.

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.

Novel ionic liquid [2-Eim] HSO4 as a dual catalytic-solvent system for preparation of hexahydroquinolines under green conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (68) ◽  
pp. 55303-55312 ◽  
Author(s):  
M. Ghorbani ◽  
S. Noura ◽  
M. Oftadeh ◽  
E. gholami ◽  
M. A. Zolfigol
Keyword(s):  
Ionic Liquid ◽  
Solvent System ◽  
Hydrogen Sulfate ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Green Conditions

A novel Brønsted acidic ionic liquid 2-ethylimidazolium hydrogen sulfate, [2-Eim] HSO4, was synthesized.

Studies on Synthesis and Properties of Hydrophobic Brønsted Acidic Ionic Liquid

2014 ◽  
Vol 1033-1034 ◽  
pp. 70-75 ◽  
Author(s):  
Li Bing Ding ◽  
Han Sheng Li ◽  
Tong Hua Chu ◽  
Qin Wu ◽  
Yun Zhao ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Ionic Liquid ◽  
High Catalytic Activity ◽  
Ionization Mass ◽  
Hydrogen Sulfate ◽  
Efficient Catalyst ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Ft Ir

A hydrophobic Brønsted acidic ionic liquid 1-octyl-3-(butyl-4-sulfonate) imidazolium hydrogen sulfate ([BsImR8][HSO4]) was synthesized and characterized by fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR), electron spray ionization mass spectrometry (ESI-MS) and thermogravimetry (TG). [BsImR8][HSO4] was used as an efficient catalyst for esterification of oleic acid with methanol to biodiesel. It was founded that [BsImR8][HSO4] exhibited high catalytic activity, which is near to that of H2SO4.It was ascribed to its strong Brønsted acidity. The catalyst could maintain high activity after five cycles of use.

One-pot synthesis of β-amido ketones using Brønsted acidic ionic liquid as an efficient and reusable catalyst

2009 ◽  
Vol 87 (2) ◽  
pp. 401-405 ◽  
Author(s):  
Krishna M. Deshmukh ◽  
Ziyauddin S. Qureshi ◽  
Nitin S. Nandurkar ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Ionic Liquid ◽  
Functional Groups ◽  
Acetyl Chloride ◽  
Operating Conditions ◽  
Reusable Catalyst ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
One Pot Condensation

An efficient protocol was developed for one-pot condensation of an aldehyde, ketone, acetyl chloride, and nitriles catalyzed by a stable and reusable 1-methyl-imidazolium hydrogen sulfate ([Hmim][HSO4]) as a Brønsted acidic ionic liquid. The system tolerated a variety of functional groups affording the corresponding β-amido ketones in moderate to good yields under milder operating conditions.

Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes

2018 ◽  
Vol 21 (7) ◽  
pp. 526-532 ◽  
Author(s):  
Zahra Abdi Piralghar ◽  
Mohammad Mahmoodi Hashemi ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Chlorosulfonic Acid ◽  
Solvent Free ◽  
Aryl Aldehydes ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Aryl Aldehyde ◽  
High Yields

Aim and Objective: In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N’, N’-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. Materials and Methods: Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature. Results: The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120oC under solvent-free conditions. Conclusion: This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.

Brønsted acidic ionic liquid-catalyzed dehydrative formation of isosorbide from sorbitol: introduction of a continuous process

2017 ◽  
Vol 7 (10) ◽  
pp. 2065-2073 ◽  
Author(s):  
Jie Deng ◽  
Bao-Hua Xu ◽  
Yao-Feng Wang ◽  
Xian-En Mo ◽  
Rui Zhang ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Continuous Process ◽  
Efficient Synthesis ◽  
Acidic Ionic Liquid ◽  
Highly Efficient ◽  
Brønsted Acidic Ionic Liquid ◽  
Acidic Ionic Liquids ◽  
First Time

A highly efficient synthesis of isosorbide from sorbitol was developed using Brønsted acidic ionic liquids (BILs) as the catalyst for the first time.

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