Ionic liquid promoted simple and efficient synthesis of β-enamino esters and β-enaminones from 1,3-dicarbonyl compounds – One-pot, three-component reaction for the synthesis of substituted pyridines

2005 ◽  
Vol 83 (10) ◽  
pp. 1746-1751 ◽  
Author(s):  
Ganesan Karthikeyan ◽  
Paramasivan T Perumal
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Ammonium Acetate ◽  
Efficient Synthesis ◽  
One Pot ◽  
Dicarbonyl Compounds ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Three Component Reaction ◽  
Substituted Pyridines

A facile enamination of 1,3-dicarbonyl compounds with amines has been developed that affords good to excellent yields of β-enamino esters and β-enaminones using Brønsted acidic ionic liquid 1-methylimidazolium trifluoroacetate ([Hmim]+Tfa–) at room temperature. This methodology has been extended for the synthesis of substituted pyridines in excellent yield by a one-pot, three-component reaction of 1,3-dicarbonyl compounds, ammonium acetate, and alkynone in the presence of [Hmim]+Tfa–.Key words: ionic liquid, β-enaminones, β-enamino esters, 1,3-dicarbonyl compounds, amines, pyridines.

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.

Aqueous, One-Pot, Three-Component Reaction for Efficient Synthesis of 2-[4-(Arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, ‑1H-benzimidazole, or -1,3-benzoxazole Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (17) ◽  
pp. 2295-2298
Author(s):  
Kommula Dileep ◽  
M. Murty
Keyword(s):  
Room Temperature ◽  
Efficient Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
Aqueous Conditions

A simple and efficient synthetic protocol has been developed involving a one-pot three-component reaction of a 2-chlorobenzazole, piperazine, and an arenesulfonyl chloride under aqueous conditions at room temperature in the absence of a catalyst, ligand, or base. By using this protocol, a variety of 2-[4-(arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, -1H-benzimidazole, and -1,3-benzoxazole derivatives were synthesized in excellent yields.

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.

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.

CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2191-2199 ◽  
Author(s):  
Yongde Zhao ◽  
Shengqiang Guo ◽  
Yang Zhou ◽  
Bencai Dai ◽  
Cuimeng Huo ◽  
...  
Keyword(s):  
Catalytic System ◽  
Sodium Azide ◽  
Room Temperature ◽  
Green Solvent ◽  
Efficient Synthesis ◽  
One Pot ◽  
Highly Efficient ◽  
Three Component Reaction ◽  
Efficient Route ◽  
Terminal Acetylenes

A concise one-pot three-component reaction of organic halides­, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.

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