Carbon–SO3H: a novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]

Rao, B. Maheshwar; Reddy, G. Niranjan; Reddy, T. Vijaikumar; Devi, B.L.A. Prabhavathi; Prasad, R. B. N.; Yadav, J. S.; Reddy, B. V. Subba

doi:10.1016/j.tetlet.2013.02.089

Cited by 84 publications

(7 citation statements)

References 41 publications

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“…Till the date lot of work has been published on synthesis of spirooxindoles and its applications in medicinally chemistry. [61] Rao et al [62]…”

Section: Synthesis Of Spiro[4h-pyran-33'-oxindole]derivativementioning

confidence: 99%

SO₃H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

Singh,

Yadav,

Bhardwaj

et al. 2023

ChemistrySelect

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Due to their fascinating biological features, heterocyclic compounds and their derivatives have long been recognized as promising molecules with potential pharmaceutical applications. The significance of heterocyclic compounds in drug discovery and development is evident from the fact that a majority of drugs in the pharmaceutical market incorporate heterocyclic compounds as active substances or ingredients. Various synthetic methods and advancements have been devised to prepare these heterocyclic compounds using diverse catalysts under mild reaction conditions. SO3H functionalized carbon material (C‐SO3H) is heterogeneous green solid catalyst that has been employed to catalyze diverse organic reactions including construction of three‐, four‐, five‐, six‐member and fused heterocycles as well as other open chain organic transformations. The C‐SO3H catalyst works under relatively mild reaction conditions and recovered from the reaction mixtures for reuse. Various cheap carbon sources covering natural organic carbon matter and industrial waste already being used to synthesize SO3H‐functionalized acidic carbon catalyst for replacement of various homogeneous acid catalysts. The present review aims to highlight the organic reactions especially those connecting for heterocyclic synthesis catalyzed by sulfonated carbons (C‐SO3H) from 2010 to till date.

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“…Till the date lot of work has been published on synthesis of spirooxindoles and its applications in medicinally chemistry. [61] Rao et al [62]…”

Section: Synthesis Of Spiro[4h-pyran-33'-oxindole]derivativementioning

confidence: 99%

SO₃H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

Singh,

Yadav,

Bhardwaj

et al. 2023

ChemistrySelect

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“…In order to minimize bio‐waste i. e. bio‐glycerol/glycerol‐pitch produced from biodiesel and fat splitting industries, we have reported a sustainable methodology for the development of a cost effective heterogeneous novel carbon‐based sulfonated acid catalysts (carbon‐SO 3 H) bearing −SO 3 H, −COOH and phenolic −OH groups [43,44] . These catalysts demonstrated their effectiveness towards the esterification of fatty acids to biodiesel as well as for different organic reactions [45] . Latter, the carbon‐SO 3 H catalyst was modified to its sodium salt as a solid base catalyst (carbon‐SO 3 Na) by treating with aqueous sodium hydroxide under controlled conditions [46] .…”

Section: Introductionmentioning

confidence: 99%

“…[43,44] These catalysts demonstrated their effectiveness towards the esterification of fatty acids to biodiesel as well as for different organic reactions. [45] Latter, the carbon-SO 3 H catalyst was modified to its sodium salt as a solid base catalyst (carbon-SO 3 Na) by treating with aqueous sodium hydroxide under controlled conditions. [46] Based on structural characterization, the carbon-SO 3 Na catalyst was found to be non-porous by its low BET surface area of 6.5 m 2 /g with sodium content of 6.73 %.…”

Section: Introductionmentioning

confidence: 99%

Carbon‐SO₃Na Catalysed Synthesis of Glycerol Carbonate via Transesterification of Glycerol and Dimethyl Carbonate

2022

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Glycerol, a major by-product from biodiesel industry valorized into glycerol carbonate (GC) employing heterogeneous carbonbased sulfated sodium (carbon-SO 3 Na) catalyst derived from glycerol. Investigations have been conducted to study the influence of reaction parameters such as catalyst dosage, DMC/ glycerol molar ratio, reaction temperature and reaction time for the production of GC in high yield with high selectivity from glycerol and dimethyl carbonate (DMC) via transesterification process. Under optimized conditions the maximum GC yield (> 99 %) with 100 % selectivity was observed with catalyst dose of 1.5 wt.% (of glycerol), DMC/glycerol molar ratio of 3 : 1, reaction temperature of 80 °C in 3 h of reaction period. Further, the catalyst was easily recovered from reaction mixture and reused without any pre-treatment. The catalyst maintained its crystalline nature with remarkable performance even after 5 cycles of reaction without any deactivation and leaching. The main advantage of the adopted carbon-SO 3 Na catalyzed protocol for the synthesis of GC is environmentally benign due to its high yield and selectivity under mild reaction conditions. Thus, the carbon-SO 3 Na catalyst has a wide utility as a potential heterogeneous solid base catalyst for several organic transformations.

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“…Spirooxindole derivatives such as are biologically‐attractive heterocycles which can be found in alkaloids and pharmaceuticals. The synthesis of these compounds is an appealing target in the organic synthesis due to their diverse biological activities including fungicidal, anticonvulsant, herbicidal and anti‐cancer properties . Spirooxindoles can also be used as a key intermediate for the synthesis of clinical pharmaceuticals .…”

Section: Introductionmentioning

confidence: 99%

“…To date many attempts have been devoted to disclose efficient protocols for the synthesis of spirooxindoles. In this line, the utilities of many catalysts such as triethylamine, piperidine, ethylenediamine diacetic acid, L‐Proline, chiral phoshoic acid and potassium tetrachloroaurate trihydrate have been proved …”

Section: Introductionmentioning

confidence: 99%

HPA decorated Halloysite Nanoclay: An efficient catalyst for the green synthesis of Spirooxindole derivatives

Sadjadi

Heravi

Malmir

et al. 2017

Applied Organom Chemis

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A novel heterogeneous catalyst, HPA@HNTs‐IMI‐SO3H, was designed and synthesized based on functionalization of halloysite nanotubes with ionic liquid and subsequent incorporation of heteropolyacid. The structure of the catalyst was studied and confirmed by using SEM/EDX, FTIR, XRD, ICP‐AES, TGA, DTGA and BET. Moreover, the catalytic activity of HPA@HNTs‐IMI‐SO3H was investigated for promoting ultrasonic‐assisted three‐component reaction of isatines, malononitrile or cyanoacetic esters and 1,3‐dicarbonyl compounds to afford corresponding spirooxindole in high yields and short reaction time. The reusability of the catalyst was also studied. Notably, the catalyst could be recovered and reused for three reaction runs. However, reusing for fourth reaction runs led to the decrease of the catalytic activity. Considering leaching test results, that observation was attributed to the leaching of heteropolyacids, which can be induced by ultrasonic irradiation.

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Carbon–SO3H: a novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]

Cited by 84 publications

References 41 publications

SO₃H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

SO₃H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

Carbon‐SO₃Na Catalysed Synthesis of Glycerol Carbonate via Transesterification of Glycerol and Dimethyl Carbonate

HPA decorated Halloysite Nanoclay: An efficient catalyst for the green synthesis of Spirooxindole derivatives

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Carbon–SO3H: a novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]

Cited by 84 publications

References 41 publications

SO3H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

SO3H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

Carbon‐SO3Na Catalysed Synthesis of Glycerol Carbonate via Transesterification of Glycerol and Dimethyl Carbonate

HPA decorated Halloysite Nanoclay: An efficient catalyst for the green synthesis of Spirooxindole derivatives

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Product

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SO₃H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

SO₃H‐Functionalized Carbon Materials: A Versatile and sustainable heterogeneous Catalyst for Diverse Organic Transformations

Carbon‐SO₃Na Catalysed Synthesis of Glycerol Carbonate via Transesterification of Glycerol and Dimethyl Carbonate