scholarly journals Long-chain Brønsted Acidic Ionic Liquids Catalyzed one-pot three-component Biginelli Reaction under Solvent-Free Conditions

2019 ◽  
Vol 2 (2) ◽  
Author(s):  
Leqin He
Keyword(s):  
Ionic Liquids ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Catalytic Performance ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Acidic Ionic Liquids ◽  
Halogen Free ◽  
Long Chain

A series of halogen-free quaternary ammonium Brønsted acidic ionic liquids (ILs) were prepared and used for Biginelli reaction among aromatic aldehydes, urea or thiourea and β-dicarbonyl compounds. The influencing factors, such as the type and amount of catalyst, solvent, reaction time and reaction temperature, were investigated. The results demonstrated that the 3-(N,N-dimethylhexadecylammonium) propanesulfonic acid toluene sulfate ([DHPA][Tos]) provide the best catalytic activity, with good catalytic performance and reusability under solvent-free conditions. A possible mechanism that accounted for the [DHPA][Tos]-catalyzed reaction was proposed.

Long-chain Brønsted acidic ionic liquids catalyzed one-pot three-component Biginelli reaction

2020 ◽  
Vol 17 (1) ◽  
pp. 21-26 ◽  
Author(s):  
Leqin He ◽  
Shenjun Qin ◽  
Jianjun Liu ◽  
Wei Zhao ◽  
Tao Chang
Keyword(s):  
Ionic Liquids ◽  
Biginelli Reaction ◽  
Reaction System ◽  
Aromatic Aldehydes ◽  
Product Yield ◽  
Ionization Mass ◽  
One Pot ◽  
Content Type ◽  
Solvent Free Conditions ◽  
Acidic Ionic Liquids

Purpose From the atom economy and environmentally friendly point of views, the development of clean and green approaches using ionic liquids (ILs) as recyclable catalysts has attracted increasing attention. The purpose of this study is to investigate the effect of task-specific ILs content on the one-pot three-component Biginelli reaction. Design/methodology/approach A series of halogen-free quaternary ammonium ILs functionalized with –SO3H group were prepared and characterized by 1H nuclear magnetic resonance (NMR), 13C NMR and electrospray ionization mass spectrometry. The ILs were used as catalysts for Biginelli reaction among aromatic aldehydes, urea or thiourea and β-dicarbonyl compounds. Anions and cations of ILs were varied to observe their effects on and contributions to the catalysts. The influencing factors, such as the amount of catalyst, solvent, reaction time and reaction temperature, were investigated. Findings The effect and contribution of cations of ILs were observed. Results showed that 3-(N, N-dimethylhexadecylammonium) propanesulfonic acid toluene sulfate ([DHPA][Tos]) showed comparable catalytic activity. Good adaptability to the reaction substrate and maximum product yield was observed when [DHPA][Tos] was used as catalyst. It was found that Biginelli reaction catalyzed by 10 mol% [DHPA][Tos] for 3 h under solvent-free conditions at 80 °C gave the best yield of 94%. Post-processing steps were simple, and the catalyst could be reused easily. Originality/value This paper demonstrates that ILs containing a long carbon chain and a bulky Tos anion efficiently promoted the reaction, in which the long carbon chains facilitate mass transfer in the reaction system.

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 Pumice as a Novel Nature Heterogeneous Catalyst for Synthesis of 3,4-dihydropyrimidine-2-(1H)-Ones/Thiones via Biginelli Reaction under Solvent-free Conditions

2021 ◽  
Author(s):  
Ali Mohamed ◽  
Lamya H. Al-Wahaibi ◽  
Antar Abdelhamid ◽  
Sayed Saber ◽  
Nadia Kanzi
Keyword(s):  
Heterogeneous Catalyst ◽  
Ethyl Acetoacetate ◽  
Biginelli Reaction ◽  
Thermal Conditions ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
One Pot ◽  
Acetyl Acetone ◽  
Solvent Free Conditions ◽  
Work Up

Abstract: An efficient and environmentally Pumice as a new catalyst for designing of 3,4- dihydropyrimidin-2(1H) ones / thiones via one-pot multi component condensation of aromatic aldehydes, urea/ thiourea and ethyl acetoacetate or acetyl acetone in excellent yields (96-99 %). The advantages using of this new catalyst is very cheap, available, non-toxic, stable under thermal conditions, easy work-up, improved yields, the product of reaction is very pure without using chromatographic methods and solvent free conditions.

One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Acidic Ionic Liquids Under Solvent-Free Conditions

2009 ◽  
Vol 39 (19) ◽  
pp. 3436-3443 ◽  
Author(s):  
Jianzhou Gui ◽  
Dan Liu ◽  
Chan Wang ◽  
Feng Lu ◽  
Jingzhao Lian ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Solvent Free ◽  
One Pot ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Acidic Ionic Liquids

scholarly journals Three-component reaction of β-keto esters, aromatic aldehydes and urea/thiourea promoted by caffeine, a green and natural, biodegradable catalyst for eco-safe Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives under solvent-free conditions

2018 ◽  
Vol 83 (6) ◽  
pp. 673-684 ◽  
Author(s):  
Farzaneh Mohamadpour ◽  
Mojtaba Lashkari
Keyword(s):  
Biginelli Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Solid Catalyst ◽  
One Pot ◽  
Keto Esters ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
High Yields

Caffeine was found to be a natural and green and biodegradable catalyst for the one-pot, three-component condensation Biginelli reaction of ?-keto esters, aromatic aldehydes and urea/thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives under solvent-free conditions. The remarkable features of this green procedure are high yields, short reaction times, simplicity of operation and work-up procedures, the availability and easy handling of this solid catalyst, avoidance of hazardous or toxic catalysts and organic solvents and economic availability of the catalyst.

Sign in / Sign up

Export Citation Format

Share Document