N‐Phenyltriazolinedione as an Efficient, Selective, and Reusable Reagent for the Oxidation of Thiols to Disulfides.

Christoforou, Angelos; Nicolaou, Georgia; Elemes, Yiannis

doi:10.1002/chin.200713059

Cited by 6 publications

(7 citation statements)

References 1 publication

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“…These reactions are of both synthetic and mechanistic interest . An extensive use of 1 in organic synthesis caused by its ability to be involved in a large number of easily running quantitative and selective reactions with a wide variety of active and low‐active substrates . Reagent 1 shows increased activity in [4+2]‐, [2+2]‐cycloaddition and ene reactions compared to other dienophiles, including the strongest π‐acceptor dienophile, tetracyanoethylene …”

Section: Introductionmentioning

confidence: 99%

Kinetics of the ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione with β‐pinene and 2‐carene: Temperature, high pressure, and solvent effects

Kiselev

Kornilov

Anikin

et al. 2018

Int J of Chemical Kinetics

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The data on temperature, solvent, and high hydrostatic pressure influence on the rate of the ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (1) with 2‐carene (2), and β‐pinene (4) have been obtained. Ene reactions 1+2 and 1+4 have high heat effects: ∆Hr‐n (1+2) −158.4, ∆Hr‐n(1+4) −159.2 kJ mol−1, 25°C, 1,2‐dichloroethane. The comparison of the activation volume (∆V≠(1+2) −29.9 cm3 mol−1, toluene; ∆V≠(1+4) −36.0 cm3 mol−1, ethyl acetate) and reaction volume values (∆Vr‐n(1+2) −24.0 cm3 mol−1, toluene; ∆Vr‐n(1+4) −30.4 cm3 mol−1, ethyl acetate) reveals more compact cyclic transition states in comparison with the acyclic reaction products 3 and 5. In the series of nine solvents, the reaction rate of 1+2 increases 260‐fold and 1+4 increases 200‐fold, respectively, but not due to the solvent polarity.

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Section: Introductionmentioning

confidence: 99%

Kinetics of the ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione with β‐pinene and 2‐carene: Temperature, high pressure, and solvent effects

Kiselev

Kornilov

Anikin

et al. 2018

Int J of Chemical Kinetics

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“…The stretching peak of amine group at 3321 cm −1 and the bending peak of amide bond at 1650 cm −1 were observed. 26 The formation of disulfide bond and the conjugation of PCL to PEG-cysteamine in PCL-SS-PEG were deduced by the wagging vibration of CH 2 −Sat 1270 cm −1 and the bending vibration of amide bond at 1650 cm −1 in Figure 1a. 27 The coupling of folate with PCL-PEI can be confirmed by UV−visible spectroscopy.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Multicomponent Polymeric Nanoparticles Enhancing Intracellular Drug Release in Cancer Cells

Ahmed

Liu

Pan

et al. 2014

ACS Appl. Mater. Interfaces

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Three kinds of amphiphilic copolymer, that is, poly(ε-caprolactone)-SS-poly(ethylene glycol) (PCL-SS-PEG), poly(ε-caprolactone)-polyethylenimine (PCL-PEI), and poly(ε-caprolactone)-polyethylenimine-folate (PCL-PEI-Fol) were synthesized and self-assembled into surface engineered hybrid nanoparticles (NPs). Morphological studies elucidated the stable, spherical, and uniform sandwich structure of the NPs. PCL-PEI and PCL-SS-PEG segments have introduced pH and reduction responsive characteristics in these NPs, while PCL-PEI-FA copolymers could provide specific targeting capability to cancer cells. The stimuli responsive capabilities of these NPs were carried out. Negative-to-positive charge reversible property, in response to the pH change, was investigated by zeta potential and nuclear magnetic resonance (NMR) measurements. The structure cleavage, due to redox gradient, was studied by dynamic light scattering (DLS) and transmission electron microscopy (TEM). These NPs showed controlled degradation, better drug release, less toxicity, and effective uptake in MCF-7 breast cancer cells. These multifunctional NPs showed promising potential in the treatment of cancer.

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“…As can be expected from section 3, TAD compounds are also redox-active compounds, acting as oxidants for substrates such as thiols, 268 leading to disulfide formation (Scheme 34c). Also alcohols 269 can be oxidized (Scheme 34d).…”

Section: Secondary Reaction Modes Of Tads and Important Side Reactionsmentioning

confidence: 99%

Triazolinediones as Highly Enabling Synthetic Tools

et al. 2016

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Triazolinediones (TADs) are unique reagents in organic synthesis that have also found wide applications in different research disciplines, in spite of their somewhat "exotic" reputation. In this review, we offer two case studies that demonstrate the possibilities of these versatile and reliable synthetic tools, namely, in the field of polymer science as well as in more recently emerging applications in the field of click chemistry. As the general use of triazolinediones has always been hampered by the limited commercial and synthetic availability of such reagents, we also offer a review of the available TAD reagents, together with a detailed discussion of their synthesis and reactivity. This review thus aims to serve as a practical guide for researchers that are interested in exploiting and further developing the exceptional click-like reactivity of triazolinediones in various applications.

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N‐Phenyltriazolinedione as an Efficient, Selective, and Reusable Reagent for the Oxidation of Thiols to Disulfides.

Cited by 6 publications

References 1 publication

Kinetics of the ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione with β‐pinene and 2‐carene: Temperature, high pressure, and solvent effects

Kinetics of the ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione with β‐pinene and 2‐carene: Temperature, high pressure, and solvent effects

Multicomponent Polymeric Nanoparticles Enhancing Intracellular Drug Release in Cancer Cells

Triazolinediones as Highly Enabling Synthetic Tools

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