2018
DOI: 10.1002/slct.201802639
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1,4‐Piperazinium Hydrogen Sulfate {[H‐pi]HSO4} a Novel Di‐Cationic Ionic Liquid: Synthesis, Characterization and Its Applications as a Catalyst in Various Organic Transformations

Abstract: In this work, a new nitrogen and sulfur based di‐cationic ionic liquid (IL), named 1,4‐piperazinium hydrogen sulfate ([H‐pi]HSO4), was simply synthesized from the reaction of piperazine with sulfuric acid, and then characterized with a variety of techniques, including Infrared (IR) and Nuclear Magnetic Resonance (NMR) spectroscopies, Thermo‐gravimetric analysis (TGA), Scanning Electron Microscope (SEM), and pH analysis. This new ionic liquid was employed as an efficient catalyst for the synthesis of 2,2′‐arylm… Show more

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Cited by 16 publications
(8 citation statements)
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“…This purine analogue containing triazolopyrimidines with a bridgehead nitrogen was also achieved with same combination of reacting components using catalysts such as boric acid (H 3 BO 3 ) in aqueous micellar, 139 DBU, 140 [H 2 -DABCO][H 2 PO 4 ] 2 or DABCO][ClO 4 ] 2 , 141 γ-Fe 2 O 3 @SiO 2 @[Bis-APTES]Cl 2 nanoparticles, 89 Brönsted acidic ionic liquid supported on rice husk ash (RHA-[pmim]HSO 4 ), 80 polyethylene glycol (PEG-400) in water, 142 nanoporous sodium montmorillonite clay (Na + -MMT)-modified 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate (Na + -MMT-[pmim]HSO 4 ), 31 and 1,4-piperazinium hydrogen sulfate ([H-pi]HSO 4 ). 143 A brief summary of the information regarding the reaction conditions, reaction time, yield of product, etc. of the reported methods is shown in Scheme 63 .…”
Section: Classificationmentioning
confidence: 99%
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“…This purine analogue containing triazolopyrimidines with a bridgehead nitrogen was also achieved with same combination of reacting components using catalysts such as boric acid (H 3 BO 3 ) in aqueous micellar, 139 DBU, 140 [H 2 -DABCO][H 2 PO 4 ] 2 or DABCO][ClO 4 ] 2 , 141 γ-Fe 2 O 3 @SiO 2 @[Bis-APTES]Cl 2 nanoparticles, 89 Brönsted acidic ionic liquid supported on rice husk ash (RHA-[pmim]HSO 4 ), 80 polyethylene glycol (PEG-400) in water, 142 nanoporous sodium montmorillonite clay (Na + -MMT)-modified 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate (Na + -MMT-[pmim]HSO 4 ), 31 and 1,4-piperazinium hydrogen sulfate ([H-pi]HSO 4 ). 143 A brief summary of the information regarding the reaction conditions, reaction time, yield of product, etc. of the reported methods is shown in Scheme 63 .…”
Section: Classificationmentioning
confidence: 99%
“…nanoporous sodium montmorillonite clay (Na + -MMT)-modied 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate (Na + -MMT-[pmim]HSO 4 ),31 and 1,4-piperazinium hydrogen sulfate ([H-pi]HSO 4 ) 143. A brief summary of the information regarding the reaction conditions, reaction time, yield of product, etc.…”
mentioning
confidence: 99%
“…A novel ionic liquid, named 1,4-piperazinium hydrogen sulfate ([H-pi]HSO 4 ) has been synthesized through the reaction of piperazine with sulfuric acid by Jashnani and co-workers [85] and applied it as an efficient catalyst (3.5 mol%) for the Knoevenagel-Michael reaction between dimedone and different aldehydes to synthesize bisdimedones using a mixture of water and ethanol as a solvent at reflux conditions. The reusability of catalyst up to 4 cycles, high yields of product (91%-98%), and short reaction time is the significance of this protocol (Scheme 11: Method 8).…”
Section: Synthesis Of Bisdimedones Using Miscellaneous Catalystsmentioning
confidence: 99%
“…After that, Tamboli 's research group, in 2016, reported the synthesis of a series of DCILs originated from 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) dichloride ([C 4 (MIm) 2 ]•2Cl) through the exchange of Cl − with OH − , AcO − , and HCO 3 − , and used them in the synthesis of cyclic ureas and urethanes [41]. In recent years, the preparation and use of ILs in the promotion of organic reactions has become an important part of our ongoing research program [17,[42][43][44][45][46]. Based on these experiences, the above-mentioned imidazole-based ILs attracted our attention, and we have found some contradictions in the characterization data of [C 4 (MIm) 2 ]•2Cl and [C 4 (MIm) 2 ]•2HSO 4 , especially in the number of protons in the 1 H NMR spectra.…”
Section: General Procedures For the Synthesis Of Pyrano[23-d] Pyrimidineonesmentioning
confidence: 99%