Camphorsulfonic Acid (CSA): An Efficient Organocatalyst for the Synthesis or Derivatization of Heterocycles with Biologically Promising Activities

Kaur, Gurpreet; Bala, Kiran; Devi, S. Sathya; Banerjee, Bubun

doi:10.2174/2213346105666181001113413

Cited by 43 publications

(12 citation statements)

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“…Camphorsulfonic acid, as a novel solid acidic catalyst, could be prepared by a one-step reaction of camphor powder and concentrated sulfuric acid under mild conditions, and the yield could reach 85%, which also laid a good foundation for its application (Liu et al, 2013;Kaur et al, 2018). Therefore, in this work, a small amount of camphorsulfonic acid as a cocatalyst was introduced into the reaction.…”

Section: Preparation Of Furfural Via Diimidazole Hexafluorophosphate Catalyzedmentioning

confidence: 99%

Preparation of Furfural From Xylose Catalyzed by Diimidazole Hexafluorophosphate in Microwave

et al. 2021

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In this work, functionalized alkyl imidazolium hexafluorophosphate ILs were synthesized and characterized; then, they were applied in the conversion of xylose to furfural under the microwave method. The results showed that when CnMF was used as a catalyst, an acidic environment was provided to promote the formation of furfural. In addition, the heating method, the solvent, and the different structures of cations in the ionic liquid influenced their catalytic activity. In an aqueous solution, the yield of furfural obtained using the microwave method was better than that of the conventional heating method, and the catalytic activity of diimidazole hexafluorophosphate was better than that of monoimidazole. Meanwhile, for the diimidazole hexafluorophosphate, the change of the carbon chain length between the imidazole rings also slightly influenced the yield. Finally, the optimal yield of 49.76% was obtained at 205°C for 8 min using 3,3′-methylenebis(1-methyl-1H-imidazol-3-ium), C1MF, as a catalyst. Mechanistic studies suggested that the catalytic activity of C1MF was mainly due to the combined effect of POFn (OH)3-n and imidazole ring. Without a doubt, the catalytic activity of C1MF was still available after five cycles, which not only showed its excellent catalytic activity in catalyzing the xylose to prepare the biomass platform compound furfural but also could promote the application of functionalized ionic liquids.

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Section: Preparation Of Furfural Via Diimidazole Hexafluorophosphate Catalyzedmentioning

confidence: 99%

Preparation of Furfural From Xylose Catalyzed by Diimidazole Hexafluorophosphate in Microwave

et al. 2021

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“…Heterocyclic skeletons are very common in naturally occurring bioactive compounds as well as in commercially available drug molecules [1][2][3]. Spiro-oxindoles and 4-hydroxycoumarin both moieties are very common in naturally occurring bioactive compounds [4,5]. Various synthetic benzopyran derivatives are found to possess a wide range of biological activities [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

X-ray crystal structure analysis of 5-bromospiro[indoline-3,7'-pyrano[3,2-C:5,6-C']dichromene]-2,6',8'-trione

et al. 2021

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An analog of spirooxindole[pyrano-bis-2H-l-benzopyran] derivatives namely 5-bromospiro [indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione was synthesized via one-pot pseudo three-component reaction of one equivalent of 5-bromoisatin and two equivalents of 4-hydroxycoumarin using mandelic acid as a naturally occurring organo catalyst in aqueous ethanol under reflux conditions. The synthesized compound was characterized by FT-IR, 1H NMR, 13C NMR, and HRMS data. Crystal structure was determined by using single X-ray crystallography technique. It was found that the crystals are triclinic with space group P-1, C108H60Br4N4O29S2: a = 11.8333(6) Å, b = 12.8151(6) Å, c = 17.1798(8) Å, α = 77.317(4)°, β = 74.147(4)°, γ = 66.493(5)°, V = 2280.0(2) Å3, Z = 1, T = 149.99(10) K, μ(MoKα) = 1.902 mm-1, Dcalc = 1.647 g/cm3, 11545 reflections measured (3.836° ≤ 2Θ ≤ 50.998°), 8310 unique (Rint = 0.0488, Rsigma = 0.0875) which were used in all calculations. The final R1 was 0.0622 (I > 2σ(I)) and wR2 was 0.1994 (all data). The crystal structure was solved by direct methods and refined by full-matrix least-squares procedure to a final R-value of 0.0622 for 6264 observed reflections. The crystal structure was stabilized by an elaborate system of N-H···O, O-H···O, C-H···π, and π···π interactions involving solvent molecules to form supramolecular structure.

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“…At present, scientists prefer metal-free organocatalysts in order to avoid metal contamination in the synthesized products. As a result, during the last decade, various organocatalysts have gained a great deal of attention in carrying out organic transformations under environmentally benign conditions [ 18 , 19 , 20 ]. Among many others, metal-free phase-transfer catalysts are being widely used in various organic reactions due to their ecofriendly, mild, and biocompatible nature [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles

Banik

Banerjee²,

Kaur³

et al. 2020

Molecules

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During the last two decades, tetrabutylammonium bromide (TBAB) has gained significant attention as an efficient metal-free homogeneous phase-transfer catalyst. A catalytic amount of TBAB is sufficient to catalyze various alkylation, oxidation, reduction, and esterification processes. It is also employed as an efficient co-catalyst for numerous coupling reactions. It has also acted as an efficient zwitterionic solvent in many organic transformations under molten conditions. In this review, we have summarized the recent developments on TBAB-catalyzed protocols for the efficient synthesis of various biologically promising heterocyclic scaffolds.

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Camphorsulfonic Acid (CSA): An Efficient Organocatalyst for the Synthesis or Derivatization of Heterocycles with Biologically Promising Activities

Cited by 43 publications

References 0 publications

Preparation of Furfural From Xylose Catalyzed by Diimidazole Hexafluorophosphate in Microwave

Preparation of Furfural From Xylose Catalyzed by Diimidazole Hexafluorophosphate in Microwave

X-ray crystal structure analysis of 5-bromospiro[indoline-3,7'-pyrano[3,2-C:5,6-C']dichromene]-2,6',8'-trione

Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles

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