β-Cyclodextrin as a recyclable catalyst: aqueous phase one-pot four-component synthesis of polyfunctionalized pyrroles

Karnakar, K.; Chowrasia, Rakhi; Manjari, Padma Sunitha; Domingues, Nélson; Ramesh, K.

doi:10.1039/c6ra08335h

Cited by 29 publications

(13 citation statements)

References 44 publications

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“…One-pot four-component procedure promoted by CD for the preparation of polysubstituted pyrroles 30 was reported for the first time by Konkala et al ( 2016 ) The synthesis of substituted pyrroles is complicated mainly by the occurrence of undesired polymerization reactions or lack selectivity, this protocol provided efficient and selective. The poor results obtained by using sodium dodecyl sulfate (SDS) or PEG-400, pointed out that CD did not act as a transfer phase catalyst and so the high reaction performance in its presence could be attributed to the formation of inclusion complexes within its hydrophobic cavity thereby facilitating the sequence of the reaction.…”

Section: Reaction Organocatalyzed By Cavity-containing Macrocyclic Scmentioning

confidence: 99%

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

et al. 2018

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In the last decades many efforts have been devoted to design supramolecular organocatalysts able to work in water as the reaction medium. The use of water as solvent provides promising benefits with respect to environmental impact. In this context, macrocyclic compounds played a role of primary importance thanks to their ease of synthesis and their molecular recognition abilities toward the reactants. The aim of this review is to give an overview of the recent advances in the field of supramolecular organocatalysis in water, focusing the attention on calixarene and cyclodextrins derivatives. Calixarenes and cyclodextrins, thanks to their hydrophobic cavities, are able to host selectively the substrates isolating they from the reaction environment. In addition, the synthetic versatilities of these macrocycles permits to introduce useful functional groups in close proximity of the hydrophobic binding sites. Regarding the cyclodextrins (CDs), we have here reviewed the their most recent uses as organocatalysts for the synthesis of heterocyclic compounds, in multi-component reactions and in carbon-carbon bond forming reactions. Examples have been reported in which CD catalysts are able to drive the regiochemistry of common organic reactions. In addition, cyclodextrins bearing catalytically active chiral groups, have shown excellent enantioselectivity in the catalysis of organic reactions. Recently reported results have shown that calixarene derivatives are able to accelerate organic reaction under “on-water” conditions with a significant selectivity toward the reactants. Under “on-water conditions” the hydrophobic effect, induced by insoluble calixarene derivatives, forces the reactants and the catalyst to aggregate and thus accelerating the reaction between them thanks to an amplification of weak secondary interactions. Regarding the use of water-soluble calixarene organocatalysts, we have here reviewed their role in the acceleration of common organic reactions.

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Section: Reaction Organocatalyzed By Cavity-containing Macrocyclic Scmentioning

confidence: 99%

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

et al. 2018

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“…Very recently, Konkala et al . reported for the first time a green method for the synthesis of polysubstituted pyrroles 13 in the presence of β‐CD as an efficient and reusable supramolecular catalyst in aqueous media at 70–80°C within 8 h to afford the products 13 in excellent yields (Scheme ) . In order to find the optimum reaction conditions, the reaction was carried out between benzaldehyde 11 , nitromethane 12 , aniline 1, and acetylacetone 3 in the presence of different catalysts and solvents at various temperatures.…”

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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“…These were synthesized through Paal-Knorr condensation reaction, Knorr reaction and Hantzsch reaction. 26 Herein we decided to study the preparation of polysubstituted pyrrole derivatives with various substituents from the reaction of aromatic aldehydes, ethyl acetoacetate, nitromethane and aniline under solvent-free conditions using Cu@imine/Fe 3 O 4 MNPs as a new, eco-friendly, reusable and promising heterogeneous nanocatalyst. Although numerous methods have been utilized for the preparation of polysubstituted pyrrole derivatives, some of these strategies suffer from disadvantages such as use of high temperature, the need for excess amounts of the catalyst, long reaction times, and need for microwave or ultrasound irradiation.…”

Section: Introductionmentioning

confidence: 99%

An efficient and recyclable nanocatalyst for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives

et al. 2019

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β-Cyclodextrin as a recyclable catalyst: aqueous phase one-pot four-component synthesis of polyfunctionalized pyrroles

Abstract: An elegant, mild and straightforward methodology was explored for the first time towards the synthesis of polyfunctionalized pyrroles using β-cyclodextrin as a reusable supramolecular catalyst in aqueous medium.

Cited by 29 publications

References 44 publications

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

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

An efficient and recyclable nanocatalyst for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives

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