Synthesis of phthalimides, isoindolin-1-ones and isoindolines bearing aminobenzoic acids as a new fluorescent compounds

Solis-Santos, Melchor; Ordóñez, Mario; Ochoa-Terán, Adrían; Morales-Cueto, Rodrigo; Labastida-Galván, Victoria

doi:10.1016/j.jphotochem.2021.113185

Cited by 4 publications

(3 citation statements)

References 51 publications

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“…The absolute values were calculated using standard samples (anthracene) that have fixed with fluorescence quantum yield reported. [22] General procedure for N-acylated 1,5-DS-T 15 a-k (GP1)…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of 1,5‐Disubstituted Tetrazole−Indolizine Bis‐Heterocycles and Their Copper (II) Recognizing Properties

et al. 2022

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A novel bis‐heterocyclic system encompassing the 1,2‐dihydro‐3H‐pyrrolo[3,4‐b]indolizin‐3‐one and 1,5‐disubstituted tetrazole moieties was designed, synthesized, and evaluated as a Copper (II) recognizing agent. This was achieved by exploiting the optical characteristics of indolizine and the copper recognizing activity of tetrazoles. For the preparation of these compounds, a novel and simple synthetic strategy consisting in a double one‐pot process involving four‐step reactions was developed. The first process is a one‐pot five component reaction by using propargylamine as a bifunctional reactant to access the key intermediate, the N‐acylated tetrazole. Consequently, N‐acylated tetrazole was subjected to a one‐pot three component reaction, consisting in a bimolecular nucleophilic substitution followed of a domino process to afford the target compounds. The photophysical properties of the obtained bis‐heterocycles were evaluated against copper (II) addition.

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Section: Methodsmentioning

confidence: 99%

“…The result is a straight line with gradient proportional to the quantum yield. The absolute values were calculated using standard samples (anthracene) that have fixed with fluorescence quantum yield reported [22] …”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1,5‐Disubstituted Tetrazole−Indolizine Bis‐Heterocycles and Their Copper (II) Recognizing Properties

et al. 2022

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“…Although the methods currently reported in the literature for the synthesis of isoindolin-1-one derivatives have several advantages, there are also disadvantages, such as the need for metal reagents, strong acids or bases, or multiple synthetic steps. [14,[16][17][18][19][20][21][22][23][24] Owing to the high value of isoindolin-1-one derivatives, the demand for developing green synthetic methods for isoindolin-1-one derivatives is increasing.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Benzyl-3-(2-oxo-2-phenylethyl)isoindolin-1-one Derivatives in Water under Catalyst-Free Conditions

Xie

Jin

et al. 2023

Synthesis

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Isoindolin-1-one derivatives, which are nitrogen-containing heterocycles, are important key intermediates for many useful organic compounds and natural products. To date, there are no syntheses for these compounds that proceed under mild reaction conditions. Therefore, in this study, we developed a catalyst-free synthesis of a series of isoindolinone derivatives involving a three-component reaction in water using o-formylbenzoic acid, benzylamine, and acetophenone as raw materials. An investigation of the influence of solvent type, substrate molar ratio, temperature, and time on the reaction revealed that the reaction proceeded optimally in water at 70 °C over 12 h. Under the optimal conditions, isoindolinone derivatives were obtained in up to 96% yield. The reaction is applicable to 20 types of substrates, and the yields were all approximately 90%. This method has the advantages of mild reaction conditions, environmental friendliness, and a broad substrate scope.

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Insights into synthesis, reactivity, and biological activity of N-isoindoline-1, 3-diones heterocycles: a systematic literature review

Ou-Ichen,

Boussetta,

Ouchetto

et al. 2024

J IRAN CHEM SOC

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Synthesis of phthalimides, isoindolin-1-ones and isoindolines bearing aminobenzoic acids as a new fluorescent compounds

Cited by 4 publications

References 51 publications

Synthesis of 1,5‐Disubstituted Tetrazole−Indolizine Bis‐Heterocycles and Their Copper (II) Recognizing Properties

Synthesis of 1,5‐Disubstituted Tetrazole−Indolizine Bis‐Heterocycles and Their Copper (II) Recognizing Properties

Synthesis of 2-Benzyl-3-(2-oxo-2-phenylethyl)isoindolin-1-one Derivatives in Water under Catalyst-Free Conditions

Insights into synthesis, reactivity, and biological activity of N-isoindoline-1, 3-diones heterocycles: a systematic literature review

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