Kinetics and mechanism of isatin ring opening in aqueous binary mixtures of methanol and acetonitrile cosolvents

Ismail, Amel M.; Zaghloul, Adel

doi:10.1002/(sici)1097-4601(1998)30:7<463::aid-kin2>3.0.co;2-q

Cited by 18 publications

(2 citation statements)

References 18 publications

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“…It was also observed that in the presence of ethanol and ethylene glycol the rate of hydrolysis decreases 348 . The effects of other solvents 349 , as well as the photophysics 350 of the hydrolysis reaction of isatin have also been studied.…”

Section: Oxygen Sulfur and Phosphorous Nucleophilesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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Section: Oxygen Sulfur and Phosphorous Nucleophilesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

View full text Add to dashboard Cite

show abstract

“…[2][3][4][5] Isatin has special properties due to the fact that it possess many reactive centers, so it undergoes electrophilic aromatic substitution (S E Ar) at carbon atoms on positions five and seven of the phenyl ring., It has been reported that isatin underwent condensation with primary amine and with active methylene compounds such as malononitrile CH 2 (CN) 2 or ethyl cyanoacetate (NCCH 2 COOC 2 H 5 ) on C-3 carbonyl group. 6 Additionally, isatin showed ring opening via nucleophilic attack on C-2 amide group by secondary amine or negatively charge ions such as HO À in which H 2 O must be present, 7,8 or ring expansions as well as spiro-annulations. The rates of hydrolysis of isatins derivatives showed a complex dependence upon pH indicative of subtle changes in mechanisms and rate-limiting step.…”

Section: Introductionmentioning

confidence: 99%

Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol

El-Rahman,

Ibrahim,

Fathalla

et al. 2023

Progress in Reaction Kinetics and Mechanism

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The reactions of 5- and 7-substituted isatin derivatives (H, Me, Cl, Br) with piperidine in 80% aqueous methanol gave the corresponding 1-(2’-amino-5’- or 3’- substituted phenyl)-2-(piperidin-1-yl) ethane-1,2-dione derivatives. The reaction is proceeded through nucleophilic attack on C-2 followed by ring opening process. The reaction showed a second order and the isokinetic temperature is 169 K indicating that the reaction is entropy controlled. The constant ∆G# value, the linear plot of ∆H# versus ∆S#, plot of log kN values at high temperature versus those at low temperatures indicated that a unified mechanism of the reactions for all substituents. The σo-Taft's constants are linearly correlated with log kN values and the ρ values are (2.01–1.86) pointing out that inductive effect of substituent is predominant and the rate-limiting is the breakdown of the tetrahedral intermediate T− and the ring opening is catalyzed by water.

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Kinetics of Malachite Green Fading in Water‐ethanol‐1‐propanol Ternary Mixtures

Samiey

Zafari

2012

J Chinese Chemical Soc

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The rate constant of malachite green (MG + ) alkaline fading was measured in water-ethanol-1-propanol ternary mixtures. This reaction was studied under pseudo-first-order conditions at 283-303 K. It was observed that the reaction rate constant increases in the presence of different weight percentages of ethanol and 1-propanol. The fundamental rate constants of MG + fading in these solutions were obtained by SESMORTAC model. In each series of experiments, concentration of one alcohol was kept constant and the concentration of the second one was changed. It was observed that at constant concentration of one alcohol and variable concentrations of the second one, with increase in temperature, k 1 values increase and this indicates that presence of ethanol (or 1-propanol) increases dissolution of 1-propanol (or ethanol) in the activated complex formed in these solutions. Also, in each zone, fundamental rate constants of reaction at each certain temperature change as k k k 2 1 1 >> >> -.

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Kinetics and mechanism of isatin ring opening in aqueous binary mixtures of methanol and acetonitrile cosolvents

Cited by 18 publications

References 18 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Entropy controlled reaction of piperidine with isatin derivatives in 80% aqueous methanol

Kinetics of Malachite Green Fading in Water‐ethanol‐1‐propanol Ternary Mixtures

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