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Ramamoorthy, V.; Ramasubbu, A.; Muthusubramanian, Shanmugam; Sivasubramanian, S.

doi:10.1023/a:1008044226549

Cited by 7 publications

(6 citation statements)

References 10 publications

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“…The association constants of such complexes involving substituted R-phenyl-N-phenyl nitrones with β-CD were reported in a study of 1,3-dipolar cycloaddition reactions of nitrones with olefins. 10 Recently, Karoui et al have shown that the half-life of the spin adduct formed during the trapping of superoxide by 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO) underwent a 7-fold increase upon addition of RM-β-CD (randomly methylated β-cyclodextrin). 11 The action of biological reducing agents (glutathione peroxidase, ascorbate) on the inclusion complex formed between the DEPMPO-superoxide adduct and RM-β-CD was impeded.…”

Section: Introductionmentioning

confidence: 99%

NMR Investigations of the β-Cyclodextrin Inclusion of (α-Phenyl-N-tert-butylnitrone) Analogues

et al. 2004

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Recently, cyclodextrin derivatives were reported to increase significantly the half-life of the spin adducts resulting from the trapping of free radicals with nitrones. To address the physicochemical characteristics of these complexes, a series of α-phenyl-N-tert-butylnitrone (PBN) analogues containing hydroxy groups on the tert-butyl group was prepared. The influence of the substitution on the supramolecular complexation of the nitrones with natural β-cyclodextrin was studied by NMR spectroscopy. 1D-NMR studies indicated a 1:1 stoichiometry and binding constants in the range 32 to 1075 M-1 depending on the substitution pattern. 2D-NMR experiments suggested a competitive inclusion of the PBN derivatives by the aryl moiety through the two accessible wide and narrow rims of the cyclodextrin.

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Section: Introductionmentioning

confidence: 99%

NMR Investigations of the β-Cyclodextrin Inclusion of (α-Phenyl-N-tert-butylnitrone) Analogues

et al. 2004

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“…In complex, the new peaks were found and shift in peak position also found where as the physical mixture has peaks which are superimposition of two individuals. The intensity of certain peaks in the complex are also enhanced thereby confirming complex formation …”

Section: β‐Cyclodextrin Catalyzed Organic Transformationsmentioning

confidence: 82%

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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“…In fact, the reaction does not take place using 1 or 2 equiv of α-CD (Table , entries 2–4), probably because the small cavity is not able to form inclusion complexes with the substrates. Of course, β-CD is able to include in its cavity both the nitrone and the dipolarophile, singularly, but when using 1 equiv, nothing happens and using 2 equiv gives only traces of cycloadducts.…”

Section: Resultsmentioning

confidence: 99%

γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water

et al. 2017

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A green and efficient 1,3-dipolar cycloaddition of nitrones with different styrenes and cinnamates using a catalytic amount of γ-cyclodextrin (γ-CD) in water has been developed to give substituted isoxazolidines. γ-CD was found to be highly efficacious in carrying out this reaction under an eco-friendly environment, affording moderate to excellent yields and, in some cases, excellent diastereomeric excess (up to >95%) at 100 °C in 8-12 h. The catalyst can be easily recuperated and recycled for several times without loss of activity. Water, an eco-friendly reaction medium, has been utilized for the first time, to the best of our knowledge, in this reaction. The credit of the presented protocol includes high yields and catalyst reusability, and precludes the use of organic solvents. The use of in silico calculations allowed us to rationalize the obtained results and to improve the stereoselectivity.

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Untitled

Cited by 7 publications

References 10 publications

NMR Investigations of the β-Cyclodextrin Inclusion of (α-Phenyl-N-tert-butylnitrone) Analogues

NMR Investigations of the β-Cyclodextrin Inclusion of (α-Phenyl-N-tert-butylnitrone) Analogues

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

γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water

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