β-Cyclodextrin mediated synthesis of 1,8-dioxooctahydroxanthenes in water

Swapna, Kokkirala; Sabbavarapu, Narayana Murthy; Yadavalli, Venkata Durga Nageswar

doi:10.5155/eurjchem.2.2.272-275.359

Cited by 37 publications

(10 citation statements)

References 39 publications

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“…= 231–233 °C, (m.p. = 230–232 °C, Swapna et al 2011), IR (KBr)/υ(cm −1 ): 2956, 1663, 1469, 1362, 1197, 1139, 846; 1 H NMR (CDCl 3, 400 MHz)/δ ppm: 7.27–7.52 (d, 2H ArH), 4.84 (s, 1H, CH), 2.51 (s, 4H, 2CH 2 ), 2.15–2.28 (q, 4H, J = 16.4 Hz, 2CH 2 ), 1.12 (s, 6H, 2CH 3 ), 0.99 (s, 6H, CH 3 ).…”

Section: Preparation Of Catalystmentioning

confidence: 99%

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A highly efficient nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a solid acid catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives

Naeimi

Nazifi

2013

J Nanopart Res

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The functionalization of silica-coated Fe3O4 magnetic nanoparticles (Fe3O4@SiO2) using chlorosulfonic acid were afforded sulfonic acid-functionalized magnetic Fe3O4 nanoparticles (Fe3O4@SiO2–SO3H) that can be applied as an organic–inorganic hybrid heterogeneous catalyst. The used Fe3O4 magnetic nanoparticles are 18–30 nm sized that was rapidly functionalized and can be used as catalyst in organic synthesis. The prepared nanoparticles were characterized by X-ray diffraction analysis, magnetization curve, scanning electron microscope, dynamic laser scattering, and FT-IR measurements. The resulting immobilized catalysts have been successfully used in the synthesis of 1,8‐dioxo-octahydroxanthene derivatives under solvent free condition. This procedure has many advantages such as; a much milder method, a shorter reaction time, a wide range of functional group tolerance, and absence of any tedious workup or purification. Other remarkable features include the catalyst can be reused at least five times without any obvious change in its catalytic activity. This procedure also avoids hazardous reagents/solvents, and thus can be an eco-friendly alternative to the existing methods.Graphical AbstractA highly efficient nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a solid acid catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivativesElectronic supplementary materialThe online version of this article (doi:10.1007/s11051-013-2026-2) contains supplementary material, which is available to authorized users.

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Section: Preparation Of Catalystmentioning

confidence: 99%

“…The residue was purified by recrystallization from ethanol. They were characterized by comparison of their physical and spectral data with those of authentic samples (Girijesh et al 2011; Mahdavinia et al 2009; Swapna et al 2011; Kantevari et al 2007). …”

Section: Preparation Of Catalystmentioning

confidence: 99%

A highly efficient nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a solid acid catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives

Naeimi

Nazifi

2013

J Nanopart Res

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“…Besides, these heterocyclic molecules have been widely used as dyes, in pH‐sensitive fluorescent materials, and laser technologies . In 2011, Kokkirala and coworkers reported an elegant and eco‐friendly method for the preparation of 1,8‐dioxooctahydroxanthenes 66 from the direct cyclocondensation of 2 mol of dimedone 57 and 1 mol of aromatic aldehydes 10 using β‐CD as a biodegradable and recyclable catalyst (Scheme ) . The products were obtained in good to excellent yields in water at 60°C.…”

Section: Application Of β‐Cd For the Synthesis Of Heterocyclesmentioning

confidence: 99%

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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“…The importance of xanthenes and acridines has been promoted by the chemists to explore new synthetic routes and protocols The methods for synthesizing xanthene using some of the catalysts of the type sulfated zirconia (SO 4 2− ZrO 2 ), nano ZrO 2 , molybdate sulfonic acid, [BiPy](HSO 3 ) 2 Cl 2 , nano titania‐supported sulfonic acid, β‐cyclodextrin, nano‐WO 3 , NbCl 5 , trichloromelamine, alumina‐sulfuric acid, ZnFe 2 O 4 , CoNP@SBA‐15, cucurbit[6]uril‐OSO 3 H, Fe 3 O 4 @SiO 2 @GMSI‐VB1‐Ni 2+ , and succinimide‐N‐sulfonic acid . 2‐Quinolone and 4‐quinolone are the importance structural moieties in medicinal molecules and they play a major role in the functioning of antibiotic drugs such as ciprofloxacin, gatifloxacin, ofloxacin, moxifloxacin, norfloxacin etc as shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

A Facile L‐Proline Catalyzed One‐Pot Synthesis of Xanthene and Acridine Based Quinolones via Knoevenagel Condensation Reaction

Reddy

Sivaramakrishna

2020

ChemistrySelect

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A highly efficient, three-component one-pot and L-proline catalyzed Knoevenagel condensation reaction of substituted-2phenoxyquinoline-3-carbaldehyde, 1,3-cyclohexanedione/dimedone or ammonium acetate is described. These reactions afford unexpected products of xanthene and acridine based quinolones in ethanol with good yields. All these isolated products are characterised by spectroscopic and analytical data.[a] M.

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β-Cyclodextrin mediated synthesis of 1,8-dioxooctahydroxanthenes in water

Cited by 37 publications

References 39 publications

A highly efficient nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a solid acid catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives

A highly efficient nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a solid acid catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives

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

A Facile L‐Proline Catalyzed One‐Pot Synthesis of Xanthene and Acridine Based Quinolones via Knoevenagel Condensation Reaction

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