Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives

2012 ◽  
Vol 67 (7) ◽  
pp. 717-724
Author(s):  
Shihua Song ◽  
Xiang Deng ◽  
Zhi Guan ◽  
Yanhong He
Keyword(s):  
Ionic Liquid ◽  
Polyethylene Glycol ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Solvent System ◽  
Environmentally Benign ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Simple Method ◽  
Peg 600

A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO3HmIm]HSO4) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

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.

2-Hydroxyethylammonium acetate as a reusable and cost-effective ionic liquid for the efficient synthesis of bis(pyrazolyl)methanes and 2-pyrazolyl-1-nitroalkanes

2012 ◽  
Vol 90 (10) ◽  
pp. 798-804 ◽  
Author(s):  
Sara Sobhani ◽  
Razieh Nasseri ◽  
Moones Honarmand
Keyword(s):  
Ionic Liquid ◽  
Michael Reaction ◽  
Scale Up ◽  
Reaction Times ◽  
Cost Effective ◽  
Environmentally Benign ◽  
One Pot ◽  
High Yields ◽  
Reaction Media ◽  
Task Specific Ionic Liquid

A new and convenient method for the synthesis of bis(pyrazolyl)methanes by one-pot tandem Knoevenagel–Michael reaction of 3-methyl-1-phenyl-5-pyrazolone with aryl, heteroaryl, or alkyl aldehydes in the presence of 2-hydroxyethylammonium acetate (2-HEAA) as a task-specific ionic liquid is described. This method was also successfully applied for the synthesis of 2-pyrazolyl-1-nitroalkanes by Michael addition of 3-methyl-1-phenyl-5-pyrazolone with β-nitrostyrenes in short reaction times. The present protocol offers several advantages such as using a reusable and cost-effective ionic liquid, an environmentally benign reaction media, being amenable to scale-up and good to high yields of the products.

scholarly journals Efficient Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones using Ionic Liquid Pyrazinium Di(hydrogen sulfate) {Py(HSO4)2} as a Novel, Green and Homogeneous Catalyst

2017 ◽  
Vol 56 (4) ◽  
Author(s):  
Abdolkarim Zare ◽  
Roghayyeh Khanivar ◽  
Marzieh Hatami ◽  
Mohammad Mokhlesi ◽  
Mohammad Ali Zolfigol ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Homogeneous Catalyst ◽  
Hydrogen Sulfate ◽  
Efficient Synthesis ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
The One ◽  
High Yields

An efficient and simple solvent-free procedure for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[<em>a</em>]-xanthen-11-one derivatives <em>via</em> the one-pot multi-component condensation of dimedone with aromatic aldehydes and β-naphthol in the presence of protic acidic ionic liquid pyrazinium di(hydrogen sulfate) {Py(HSO<sub>4</sub>)<sub>2</sub>} as a green and homogeneous catalyst is described. All reactions proceed efficiently, and the title compounds are produced in high yields and in short reaction times.

scholarly journals 1-Methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium Chloride as a New and Green Ionic Liquid Catalyst for One-Pot Synthesis of Dihydropyrimidinones under Solvent-Free Condition

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Sami Sajjadifar ◽  
Eshagh Rezaee Nezhad ◽  
Ghasem Darvishi
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Simple Method ◽  
Free Condition ◽  
Multicomponent Condensation ◽  
Acidic Ionic Liquid ◽  
Solvent Free Condition ◽  
High Yields

An efficient and simple method for the preparation of 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride{(MSEI)Cl}as an acidic ionic liquid is described. One-pot multicomponent condensation of 1,3-dicarbonyl compounds, urea/thiourea and aldehydes at 80∘C affords the corresponding compounds in high yields and in short reaction times by using (MSEI)Cl.

scholarly journals Production of 5-hydroxymethylfurfural from Japanese cedar (Cryptomeria japonica) in an ionic liquid, 1-methylimidazolium hydrogen sulfate

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Ryoya Ito ◽  
Hisashi Miyafuji
Keyword(s):  
Ionic Liquid ◽  
Cryptomeria Japonica ◽  
Steam Distillation ◽  
Maximum Yield ◽  
Reaction System ◽  
Japanese Cedar ◽  
Solvent System ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Reaction Systems

AbstractProduction of 5-hydroxymethylfurfural (5-HMF) from Japanese cedar (Cryptomeria japonica) using an ionic liquid, 1-methylimidazolium hydrogen sulfate ([MIM]HSO4), was investigated. 5-HMF can be produced from C. japonica at temperatures above 120 °C. The maximum yield of 5-HMF was about 9 wt% after 15 min of treatment at 160 °C. However, 5-HMF produced in this process tended to decompose as the treatment continued. To avoid decomposition and to provide a means of recovering 5-HMF from [MIM]HSO4, three reaction systems based on [MIM]HSO4 were investigated: biphasic [MIM]HSO4/organic solvent system, [MIM]HSO4 with vacuum distillation, and [MIM]HSO4 with vacuum steam distillation. The [MIM]HSO4 reaction system combined with vacuum steam distillation was most effective. The maximum yield of 5-HMF was 17.5 wt% after treatment for 45 min at 160 °C. The combination of [MIM]HSO4 treatment with vacuum steam distillation is suitable for 5-HMF production because it is a one-pot process without the need for catalysts or pretreatment.

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.

Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

2021 ◽  
Vol 3 (6) ◽  
Author(s):  
Kobra Nikoofar ◽  
Fatemeh Shahriyari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
H Nmr ◽  
Sonic Waves ◽  
Ft Ir ◽  
High Yields ◽  
Work Up ◽  
C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

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