ChemInform Abstract: Syntheses of Cyclic Hydroxamic Acid Derivatives, and Their Chelating Abilities and Biological Activities.

Tanaka, Kuniyoshi; Matsuo, Keizo; Nakanishi, Atsuko; Kataoka, Yasuki; Takase, Kazuko; Otsuki, Shujiro

doi:10.1002/chin.198906188

Cited by 2 publications

(3 citation statements)

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“…Hydroxamic acids are acid species but also behave as weak bases due to the NCO moiety . Despite their recognized importance, there are only a few experimental contributions on their acid−base behavior.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO₃ Solutions in Water and in Mixtures of Water and Dioxane

Fazary¹

2005

J. Chem. Eng. Data

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The protonation equilibria for nine hydroxamic acids in solutions have been studied pH-potentiometrically via a modified Irving and Rossotti technique. The dissociation constants (pK a values) of hydroxamic acids and the thermodynamic functions (ΔG°, ΔH°, ΔS°, and δ) for the successive and overall protonation processes of hydroxamic acids have been derived at different temperatures in water and in three different mixtures of water and dioxane (the mole fractions of dioxane were 0.083, 0.174, and 0.33). Titrations were also carried out in water ionic strengths of (0.15, 0.20, and 0.25) mol dm-3 NaNO3, and the resulting dissociation constants are reported. A detailed thermodynamic analysis of the effects of organic solvent (dioxane), temperature, and ionic strength on the protonation processes of hydroxamic acids is presented and discussed to determine the factors which control these processes.

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Section: Introductionmentioning

confidence: 99%

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO₃ Solutions in Water and in Mixtures of Water and Dioxane

Fazary¹

2005

J. Chem. Eng. Data

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“…In contrast to the wide range of use of aromatic hydroxamic acid derivatives, there is only limited information available on the use of alicyclic hydroxamic acids, and their reactions . In most cases, the hydroxamic moiety is built up in the last step of the synthesis .…”

Section: Introductionmentioning

confidence: 99%

“…[18] By using chiral mono-N-protected amino hydroxamic acid ligands, the first intermolecular example was reported for enantioselective functionalization of prochiral unactivated C-H bonds. [19] In contrast to the wide range of use of aromatic hydroxamic acid derivatives, [20][21][22][23][24][25][26][27][28][29] there is only limited information available on the use of alicyclic hydroxamic acids [30,31] and their reactions. [32] In most cases, the hydroxamic moiety is built up in the last step of the synthesis.…”

Section: Introductionmentioning

confidence: 99%

A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐a]isoindole Enantiomers

et al. 2016

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A simple method was developed to prepare pyrimido[2,1‐a]isoindole derivatives by using di‐endo‐ and di‐exo‐ethyl 3‐aminobicyclo[2.2.1]hept‐5‐ene‐2‐carboxylate enantiomers as chiral sources. The method is based on a domino ring‐closure reaction of norbornene 2‐aminohydroxamic acid followed by microwave‐induced retro‐Diels–Alder reaction. In the case of enantiomeric starting substances, the chirality is transferred from norbornene derivatives to pyrimido[2,1‐a]isoindoles. The configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy [based on 2D NOE cross‐peaks and 3JH,H coupling constants] and X‐ray crystallography.

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ChemInform Abstract: Syntheses of Cyclic Hydroxamic Acid Derivatives, and Their Chelating Abilities and Biological Activities.

Abstract: The N‐hydroxylactams (II), (V), (VIII), and (XI) are prepared from 2‐nitrophenylpyruvic acid (I), the azlactones (III), or the aminohydroxamic acid (VI) and (X) as shown in the reaction scheme.

Cited by 2 publications

References 1 publication

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO₃ Solutions in Water and in Mixtures of Water and Dioxane

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO₃ Solutions in Water and in Mixtures of Water and Dioxane

A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐a]isoindole Enantiomers

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ChemInform Abstract: Syntheses of Cyclic Hydroxamic Acid Derivatives, and Their Chelating Abilities and Biological Activities.

Abstract: The N‐hydroxylactams (II), (V), (VIII), and (XI) are prepared from 2‐nitrophenylpyruvic acid (I), the azlactones (III), or the aminohydroxamic acid (VI) and (X) as shown in the reaction scheme.

Cited by 2 publications

References 1 publication

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO3 Solutions in Water and in Mixtures of Water and Dioxane

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO3 Solutions in Water and in Mixtures of Water and Dioxane

A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐a]isoindole Enantiomers

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Resources

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Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO₃ Solutions in Water and in Mixtures of Water and Dioxane

Thermodynamic Studies on the Protonation Equilibria of Some Hydroxamic Acids in NaNO₃ Solutions in Water and in Mixtures of Water and Dioxane