β-Cyclodextrin as a supramolecular catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole and spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] in aqueous medium

Tayade, Yogesh A.; Padvi, Swapnil A.; Wagh, Yogesh B.; Dalal, Dipak S.

doi:10.1016/j.tetlet.2015.03.084

Cited by 102 publications

(35 citation statements)

References 48 publications

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“…They can be prepared by the reaction of indoline-2,3-dione 1 with the appropriate dibromo compounds 2a-f in the presence of anhydrous K2CO3 (Scheme 1). [35][36][37] The reactivity of 3a-c towards 3-aminocrotononitrile 4 was investigated. Thus, reaction of an AcOH solution of one equivalent of each of the bis(indoline-2,3-diones) 3a-c with four equivalents of 4 afforded the respective bis(2',6'-dimethyl-2-oxo-1'Hspiro[indoline-3,4'-pyridine]-3',5'-dicarbonitriles) 5a-c which are tethered to alkyl linkage (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Bis(indoline-2,3-diones): versatile precursors for novel bis(2',6'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile) derivatives

Abdelmoniem¹,

Elwahy²,

Abdelhamid³

2016

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Bis(indoline-2,3-diones): versatile precursors for novel bis(2',6'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile) derivatives

Abdelmoniem¹,

Elwahy²,

Abdelhamid³

2016

Arkivoc

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“…In this report, we disclosed a newer environmentally benign methodology for the synthesis of dihydropyrano[2,3‐c]pyrazoles 27 and spiro[indoline‐3,4′‐pyrano[2,3‐c]pyrazoles] 28 as one‐pot synthesis involving four component reaction of substituted aldehydes 22 and isatins 23 (2 mmol), β‐keto ester (2 mmol) 24 , malononitrile (2 mmol) 25 and hydrazine hydrate 26 (2 mmol) in the presence of β‐cyclodextrin (0.2 mmol/10 mol %) as a recyclable catalyst in aqueous media H 2 O−EtOH (9 : 1) at 80 °C. The general scheme for the synthesis of dihydropyrano[2,3‐c]pyrazoles and spiro[indoline‐3,4′‐pyrano[2,3‐c]pyrazoles] is depicted in Scheme …”

Section: β‐Cyclodextrin Catalyzed Organic Transformationsmentioning

confidence: 99%

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

Dalal

Patil

Tayade

2018

The Chemical Record

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β-Cyclodextrin is cyclic oligosaccharide possessing hydrophobic cavity, which binds the substrates selectively and catalyze number of organic transformations with high selectivity. It catalyzes the reaction by non-covalent supramolecular bonding with reversible formation of host-guest complexes as seen in enzymes. This account summarizes our efforts in designing a good number of important organic transformations using β-cyclodextrin and its derivatives. These reactions were performed in neat, aqueous as well as organic media. Greener synthetic routes to a variety of biologically relevant organic molecules has been developed. The temperature, solvent and catalyst amount plays in important role in these reactions. β-Cyclodextrin activates variety of organic compounds like aldehydes, ketones, anhydride, oximes, amines, nitriles and increases the rate of reactions.

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“…Due to their special chemical and physical properties, cyclodextrins are very useful in pharmaceuticals and food and agricultural industries [1][2][3][4][5]. Their enzyme-like hydrophobic pocket also allows it to catalyze chemical reactions just like an enzyme [6][7][8][9][10][11][12]. As a biomimetic supramolecular catalyst, β-cyclodextrins is also able to catalyze the important Diels-Alder reaction and synthesize various compounds [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

An MM and QM Study of Biomimetic Catalysis of Diels-Adler Reactions Using Cyclodextrins

Chen

Sun

Tang

et al. 2017

Preprint

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We conducted computational research to investigate the mechanism by which cyclodextrins (CDs) catalyze Diels-Alder reaction between 9-anthracenemethanol and N-cyclohexylmaleimide. Hydrogen bonds between N-cyclohexylmaleimide and the hydroxyl groups of cyclodextrins were initially thought to play an important role in the catalysis [Chaudhuri, S. et al. Tetrahedron Letters, 2015, 56, 1619-1623 Our calculations show that such hydrogen bonds, if exist, could lower the activation energy barrier for the transition state of 9-anthracenemethanol and Ncyclohexylmaleimide to some extent. However, they are not stable enough to promote the reaction. The binding of 9-anthracenemethanol and N-cyclohexylmaleimide to cyclodextrins is found to be the key to the catalysis. Cyclodextrins act as a container to hold the two reactants in the cavity, pre-organizes them for the reactions, and thus reduces the entropy penalty to the activation free energy. Dimethyl-β-CD is found to be a better catalyst for this specific reaction than β-CD because it outperforms β-CD in almost every step of catalysis. It binds Ncyclohexylmaleimide more tightly, holds both 9-anthracenemethanol and Ncyclohexylmaleimide for much longer time in its binding site, and pays smaller entropy penalty to the activation free energy of the transition state. This computational work sheds light on the mechanism of the catalytic reaction by cyclodextrins, and introduces new perspectives to the supramolecular catalysis.

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β-Cyclodextrin as a supramolecular catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole and spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] in aqueous medium

Cited by 102 publications

References 48 publications

Bis(indoline-2,3-diones): versatile precursors for novel bis(2',6'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile) derivatives

Bis(indoline-2,3-diones): versatile precursors for novel bis(2',6'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile) derivatives

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

An MM and QM Study of Biomimetic Catalysis of Diels-Adler Reactions Using Cyclodextrins

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