1,3-Disulfonic acid benzimidazolium chloride as an efficient and recyclable ionic liquid catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones

Abbasi, Mohsen

doi:10.1007/s11164-015-2211-2

Cited by 14 publications

(2 citation statements)

References 37 publications

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“…Starting from the first report by Katritzky et al [45], BILs were investigated in fields that comprise CO 2 capture and conversion [46,47], electronics [48][49][50], dye solar cells [51], anticancer and antibacterial agents [52,53], bioremediation technologies [54,55], fuel desulfurization [56], extraction [57], lignin conversion [58], and fuel cell [59,60]. On the other hand, an area in which BILs were heavily studied is organic synthesis, where they were successfully used as catalysts in several reaction classes such as the Biginelli reaction [61], the Micheal reaction [62,63], condensations [64][65][66][67], alkylations [68], amine formylation [69], coupling [70], and esterifications [71]. Furthermore, the use of BILs as catalysts has also been reported in the preparation of natural-derived building blocks: in the transesterification of castor oil with methanol [72], in the production of ethyl levulinate [73] and in the preparation of 5-hydroxymethyl furfural starting from chitosan [74].…”

Section: Introductionmentioning

confidence: 99%

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

et al. 2021

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Benzimidazole dicationic ionic liquids (BDILs) have not yet been widely explored in spite of their potential. Therefore, two structurally related families of BDILs, paired with either bromide or bistriflimide anions and bearing alkyl spacers ranging from C3 to C6, have been prepared. Their thermal properties have been studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), while their electrical properties have been assessed by cyclic voltammetry (CV). TG analysis confirmed the higher stability of the bistriflimide BDILs over the bromide BDILs, with minor variation within the two families. Conversely, DSC and CV allowed for ascertaining the role played by the spacer length. In particular, the thermal behavior changed dramatically among the members of the bistriflimide family, and all three possible thermal behavior types of ILs were observed. Furthermore, cyclic voltammetry showed different electrochemical window (C3(C1BenzIm)2/2Tf2N < C4(C1BenzIm)2/2Tf2N, C5(C1BenzIm)2/2Tf2N < C6(C1BenzIm)2/2Tf2N) as well as a reduction peak potential, shape, and intensity as a function of the spacer length. The results obtained highlight the benefit of accessing a more structurally diverse pool of compounds offered by dicationic ILs when compared to the parent monocationic ILs. In particular, gains are to be found in the ease of fine-tuning their properties, which translates in facilitating further investigations toward BDILs as designer solvents and catalysts.

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Section: Introductionmentioning

confidence: 99%

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

et al. 2021

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“…Over the past decade, several catalysts such as H 2 SO 4, [ 11 ] trifluoroacetic acid, [ 12 ] mesoporous NH 4 H 2 PO 4 /MCM‐41, [ 13 ] zeolite‐supported heteropolyacid, [ 14 ] silica‐bonded S ‐sulfonic acid, [ 15 ] silica‐bonded N ‐propyl sulfamic acid, [ 16 ] and MCM‐41‐anchored sulfonic acid, [ 17 ] potassium fluoride‐modified clay [ 18 ] LaCL 3 –graphite, [ 19 ] phytic acid, [ 20 ] bioglycerol‐based sulfonic acid functionalized carbon, [ 8 ] sulfonated carbon materials (SCM), [ 21 ] phosphor tungstic acid, [ 22 ] phthalimide‐ N ‐sulfonic acid (PISA), [ 23 ] Fe 3 O 4 NPs, [ 24 ] Hf(OTf) 4 , [ 25 ] Cu(II) metal–organic framework, [ 26 ] Punica granatum peel, [ 27 ] zeolite‐supported HPA, [ 14 ] cellulose sulfuric acid, [ 28 ] Copper(II) Sulfamate, [ 29 ] Cu–EDTA‐modified APTMS‐Fe 3 O 4 @SiO 2 , [ 30 ] BiVO 4 ‐NPs, [ 31 ] [C 16 Im][Oxa], [ 32 ] Preyssler heteropolyacid supported on silica coated NiFe 2 O 4 , [ 33 ] nanoZnO, [ 34 ] Co(NO 3 ) 2 .6H 2 O, [ 35 ] pineapple juice, [ 36 ] [Et 3 N–SO 3 H]H 2 SO 4 , [ 37 ] [Dsbim]Cl ionic liquid, [ 38 ] CF 3 SO 3 Ag, [ 39 ] [Simp]HSO 4 , [ 40 ] Fe 3 O 4 /PAA–SO 3 H [ 41 ] have been investigated to catalyze the Biginelli reaction.…”

Section: Introductionmentioning

confidence: 99%

CoNiFe₂O₄@Silica‐SO₃H nanoparticles: New recyclable magnetic nanocatalyst for the one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones/thiones under solvent‐free conditions

Karimian

Rad

Mahdavi

2020

J Chinese Chemical Soc

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A useful and green synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives were achieved by one-pot cyclocondensation between substituted aryl aldehydes, diketone/ketoester, and urea/thiourea using magnetic CoN-iFe 2 O 4 @Silica-SO 3 H nanoparticles under solvent-free condition. The choice of this approach showed essential advantages such as short reaction time, simple work-up procedure, high activity of the catalyst, high yield of the reaction products, the magnetic properties of the catalyst, and environmentally amiable conditions. In addition, the catalyst recovered and reused four times without notable loss of its activity. The magnetic CoNiFe 2 O 4 @Silica-SO 3 H nanoparticles were described by Fourier-transform infrared spectroscopy (FT-IR), field emission scanning electron microscope, energy dispersive X-ray spectroscopy, X-ray diffraction spectroscopy, and vibrating sample magnetometer. The products were obtained with excellent yields (88-98%). The formation of the products was confirmed and identified with their physical properties (melting points), the FT-IR, 1 H NMR, 13 C NMR, mass spectrometry, and the elemental analysis.

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β-Cyclodextrin as an Efficient and Recyclable Supramolecular Catalyst for the Synthesis of Heterocyclic Compounds

Abbasi

2017

Journal of the Chinese Chemical Society

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β-Cyclodextrin (β-CD), a naturally occurring supramolecular structure, is an effective catalyst for the synthesis of heterocyclic compounds. Its ubiquity, high performance, nontoxicity, ease of separation, and reusability have drawn the attention of green chemists. Here we present the synthetic procedures of heterocyclic compounds catalyzed by β-CD in water and compare them with those using organic solvents. In many cases, using water as the solvent shows better efficiency than conventional organic solvents with regard to catalytic activity and simplicity of recycling procedures. This review highlights the applications of β-CD in catalysis covering the years 2004-2016.Mohsen Abbasi was born in Jam, Bushehr, Iran,in 1989. He received the B.Sc. degree in pure chemistry from the University of Zabol in 2012, and the M.Sc. degree in organic chemistry from Ferdowsi University of Mashhad, Iran, in 2014 under the supervision of Dr. Seyed Mohammad Seyedi. His research interests include organic methodology catalysis and the application of multicomponent reactions in the synthesis of heterocyclic compounds. He has co-authored several reseach papers published in reputed journals and national conference proceedings.

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1,3-Disulfonic acid benzimidazolium chloride as an efficient and recyclable ionic liquid catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones

Cited by 14 publications

References 37 publications

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

CoNiFe₂O₄@Silica‐SO₃H nanoparticles: New recyclable magnetic nanocatalyst for the one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones/thiones under solvent‐free conditions

β-Cyclodextrin as an Efficient and Recyclable Supramolecular Catalyst for the Synthesis of Heterocyclic Compounds

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1,3-Disulfonic acid benzimidazolium chloride as an efficient and recyclable ionic liquid catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones

Cited by 14 publications

References 37 publications

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

CoNiFe2O4@Silica‐SO3H nanoparticles: New recyclable magnetic nanocatalyst for the one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones/thiones under solvent‐free conditions

β-Cyclodextrin as an Efficient and Recyclable Supramolecular Catalyst for the Synthesis of Heterocyclic Compounds

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CoNiFe₂O₄@Silica‐SO₃H nanoparticles: New recyclable magnetic nanocatalyst for the one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones/thiones under solvent‐free conditions