PEG-SO<sub>3</sub>H as a Catalyst for the Preparation of Bis-Indolyl and Tris-Indolyl Methanes in Aqueous Media

Rani, V. Jhansi; Vani, K. Veena; Rao, C. Venkata

doi:10.1080/00397911.2010.551700

Cited by 22 publications

(11 citation statements)

References 25 publications

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“…125,126 Rani et al have reported facile, efficient, and green synthesis of bis-indolyl and tris-indolyl methanes trough onepot condensation of indole with structurally diverse aldehydes and ketones in the presence of poly(ethylene glycol)-bound sulfonic acid (PEG-OSO 3 H) as catalyst at room temperature (Scheme 13a and b). 127 Electron deciency and the nature of substituents on the ring of aldehydes didn't show any obvious effects on this conversion. An electron-rich as well as electron decient aldehydes reacted with indoles with equal ease to give the products in excellent yields.…”

Section: Preparation Of Ps-peg-bound Sulfonic Acid (Ps-peg-oso 3 H) 35mentioning

confidence: 94%

Sulfonated polyethylene glycol (PEG-OSO₃H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Vekariya

2015

RSC Adv.

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The objective of this review is to summarize some of the recent advances in a sulfuric acid-modified polyethylene glycol 6000 (PEG-OSO 3 H) as a stable, recyclable and bio-degradable polymeric catalyst in organic synthesis. PEG-OSO 3 H is a highly efficient and eco-friendly catalyst, which catalyzed various organic reactions and could be recovered and reused several times without significant loss of its activity. In this review, preparation and application of PEG-OSO 3 H in organic synthesis are investigated.

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Section: Preparation Of Ps-peg-bound Sulfonic Acid (Ps-peg-oso 3 H) 35mentioning

confidence: 94%

Sulfonated polyethylene glycol (PEG-OSO₃H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Vekariya

2015

RSC Adv.

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“…Para-substituted aryl iodides afforded the desired products in 92-96% yields (entries 6-8), while aryl iodides with strong electron-deficient para-substituted phenylacetylenes (p-NO 2 or p-CF 3 ) led to reduced yields of coupling reactions of 60-80% (entries 9 and 10). Various alkynes, both aryl and aliphatic alkynes, could smoothly couple with aryl iodides, and the yields exceeded 83% (entries [11][12][13][14][15][16][17][18]. Unfortunately, the coupling reactions using bromobenzene and chlorobenzene with phenylacetylene gave 20 and 5% yields of cross-coupling products (entries 19 and 20).…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, it is promising to explore BIMs in terms of accelerating copper‐catalyzed cross‐couplings of aryl iodides and terminal alkynes. To the best of our knowledge, reports of a robust, reliable approach to obtain gram‐scale amounts of those compounds are still scarce. We are also interested in developing a reliable pathway to produce BIMs.…”

Section: Introductionmentioning

confidence: 99%

Highly modulated bisindoles: ligands for copper‐catalyzed Sonogashira reaction

Wang

et al. 2016

Applied Organom Chemis

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Bisindoles (BIMs) were modulated as powerful N,N′ donor ligands for the copper-catalyzed Sonogashira reaction. Ligand screening experiments on 11 BIM compounds found that 3,3′-(4-chlorophenyl)methylenebis(1-methyl-1H-indole) (10%) efficiently accelerated CuCl (5%)-catalyzed cross-coupling of aryl iodides with terminal alkynes. A wide range of substituted aryl iodides and/or alkyl-and aryl-substituted terminal alkynes were examined, leading to the corresponding coupling products with yields up to 99%. An efficient and scalable protocol for the synthesis of BIM ligands on a gram scale, with extremely low catalyst loading of o-ClC 6 H 4 NH 3 + Cl À , was also developed with a reaction time of 20 min with yields up to 93%. This novel N,N′ ligand was air-stable, easily available and highly modulated with low copper loading.

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“…It is previously used for the syn-thesis of B-hydroxy thiocyantes via regioselective ring opening of epoxides (Kiasat and Mehrjardi, 2008) and synthesis of triazoloindazole-triones, spiro triazoloindazole-tetraones (Hasaninejad et al, 2011). PEG-SO 3 H in aqueous media proved a good catalyst for the synthesis of Bis-indolyl and Trisindolylmethanes by condensation of indole with aldehydes (Rani et al, 2012). Recently several methods have been employed for carried out reactions in water irrespective usage of organic solvents because water is very cheap, less cost, on-lammable, and environmentally eco-friendly solvent.…”

Section: Introductionmentioning

confidence: 99%

PEG-SO3H promoted one pot grinding method for the synthesis of 2-amino-4H-chromene-3-carboxylates

Mahesh¹,

Balaji²

2020

ijrps

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There is a crucial medical need for the synthesis of 4H-chromene compounds via simple efficient methods. 4H-chromene compounds are stated to have a wide range of medicinal applications such as anti-bacterial, anti-cancer (EPC2407 and MX58151), antimalarial, antifungal, anti-rheumatic and anti-viral properties depending up on the substituents which is present on the heterocyclic compounds. Nowadays multi component protocols shows a better advantages such as better yield, less reaction time and no usage of different solvents for synthesis of biological important heterocyclic compounds over other synthetic approaches. The operational simplicity and applicability of this protocol to various analogues make it an alternative to previous reported methods.Therefore, this work was to prepare a series of 4H-chromene analogues via simple method with short time. Here, we reported the synthesis of 2-amino-4H-chromene-3-carboxylates using green solvent(water) under grinding method by one pot three component reaction of substituted aldehydes, dimedone and cyano acetates. This reaction was catalysed by catalytic amount of PEG-SO3H at room temperature. This catalyst proved the efficient for synthesis of many heterocyclic compounds. This reaction proceeds with very short time i.e. 5 mins. The 2-amino-4H-chromene derivatives (4a-i) was obtained with excellent yields(85-94%).

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PEG-SO₃H as a Catalyst for the Preparation of Bis-Indolyl and Tris-Indolyl Methanes in Aqueous Media

Cited by 22 publications

References 25 publications

Sulfonated polyethylene glycol (PEG-OSO₃H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Sulfonated polyethylene glycol (PEG-OSO₃H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Highly modulated bisindoles: ligands for copper‐catalyzed Sonogashira reaction

PEG-SO3H promoted one pot grinding method for the synthesis of 2-amino-4H-chromene-3-carboxylates

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PEG-SO3H as a Catalyst for the Preparation of Bis-Indolyl and Tris-Indolyl Methanes in Aqueous Media

Cited by 22 publications

References 25 publications

Sulfonated polyethylene glycol (PEG-OSO3H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Sulfonated polyethylene glycol (PEG-OSO3H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Highly modulated bisindoles: ligands for copper‐catalyzed Sonogashira reaction

PEG-SO3H promoted one pot grinding method for the synthesis of 2-amino-4H-chromene-3-carboxylates

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PEG-SO₃H as a Catalyst for the Preparation of Bis-Indolyl and Tris-Indolyl Methanes in Aqueous Media

Sulfonated polyethylene glycol (PEG-OSO₃H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

Sulfonated polyethylene glycol (PEG-OSO₃H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances