A comprehensive survey upon diverse and prolific applications of chitosan-based catalytic systems in one-pot multi-component synthesis of heterocyclic rings

International Journal of Biological Macromolecules, Год журнала: 2021, Номер 186, С. 1003 - 1166

Опубликована: Июнь 24, 2021

Язык: Английский

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Aggregation-Induced Emission: From Small Molecules to Polymers—Historical Background, Mechanisms and Photophysics

Topics in Current Chemistry, Год журнала: 2021, Номер 379(3)

Опубликована: Март 16, 2021

Язык: Английский

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Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(9)

Опубликована: Июль 29, 2023

Abstract Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, use transition metal catalysts or additives MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest metal‐free N ‐heterocyclic compounds. This review provides comprehensive concise overview advancements valuable ‐heterocycles over past five years. The is systematically organized, categorizing discussed based on size heterocyclic ring number nitrogen atoms. Only that result formation rings containing at least one atom are included, while derivatization using falls outside scope this review. By highlighting developments field, aims showcase potential significance sustainable strategies accessing elimination metals not only simplifies reaction conditions but also contributes greener more environmentally friendly approaches. serves resource researchers interested design application

Язык: Английский

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Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review

RSC Advances, Год журнала: 2025, Номер 15(13), С. 9676 - 9755

Опубликована: Янв. 1, 2025

The tremendous potential of transition metal-free multi-component reactions (MCR) in the synthesis N-heterocyclic frameworks is examined this review, offering a complete overview subject matter. discussion on mechanistic rationale reaction routes and intermediates provides profound insights into underlying changes, encouraging deeper investigation various molecular frameworks. This review serves as doorway to study practicality exploiting these for efficient uncomplicated specific nitrogen heterocycles. Specifically, we reveal catalysts field. Because their extensive scope diversity, enable heterocycles that contain nitrogen, which include 5-membered (carbazole, pyrimidines, pyrroles) 6-membered rings (piperidine, pyridine, quinoline, diazinane, pyrazine, quinoxaline, 1,2,3-triazine). In addition, compatibility with functional groups substrates not only increases synthetic value compounds but also broadens relevance domains medical chemistry, materials science, other relevant areas study. To motivate future development field, successful examples described highlight powerful instruments quick general, thorough insightful examination catalysts, highlighting contemporary organic revolutionize field heterocycle synthesis.

Язык: Английский

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Direct Introduction of −OCD₃ into the Hantzsch Pyrrole Synthesis via Multicomponent Cascade Cyclization: Synthesis of Fully Substituted Pyrrole Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(17), С. 2888 - 2893

Опубликована: Июль 25, 2023

Abstract A I 2 ‐DMSO mediated approach to introduce −OCD 3 into pyrroles in situ via multicomponent cascade cyclization reaction using methyl ketones, aniline, ethyl benzoylacetate and CD OD as readily available substrates is reported. This process realizes introduction of the Hantzsch pyrrole synthesis deuterated alkoxy‐substituted with formation one C−C bond, C−O bond two C−N bonds pot. Notably, this conversion has good substrate compatibility (62 examples) eliminates need for anhydrous anaerobic operation.

Язык: Английский

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Aromaticity-Enhanced pH-Responsive Electrochemiluminescence of Cyclopentadienols

Analytical Chemistry, Год журнала: 2022, Номер 94(15), С. 6036 - 6043

Опубликована: Апрель 6, 2022

Due to significantly tackling the problems of aggregation-caused quenching and water insolubility, aggregation-induced emission electrochemiluminescence (AIE-ECL) has emerged as a research highlight in aqueous detection sensing. Herein, we reported series cyclopentadienols featuring excellent AIE-ECL properties on basis an enhanced aromaticity strategy. In detail, substituents profoundly determined ECL by affecting characteristic absorption peak intensity ratio UV-vis spectra lowest unoccupied molecular orbital (LUMO)-highest occupied (HOMO) energies. It was found that 1,2,3,4,5-pentafluorophenyl cyclopentadienol (PFCD) containing electron-withdrawing fluorine substituent, maximum R/B band ratio, smaller LUMO-HOMO gap demonstrated best performance. Meanwhile, such system displayed wide response range toward pH (4-12) with good linear relationship. Our not only enriched polycyclic aromatic hydrocarbon-based systems but also established efficient sensor phase.

Язык: Английский

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Copper-catalyzed three-component annulation toward pyrroles via the cleavage of two C–C bonds in 1,3-dicarbonyls

Chemical Communications, Год журнала: 2023, Номер 59(71), С. 10636 - 10639

Опубликована: Янв. 1, 2023

The first copper-catalyzed three-component annulation of α,β-unsaturated ketoximes, 1,3-dicarbonyls and paraformaldehyde has been documented. This novel strategy achieved the two C-C bond cleavage 1,3-dicarbonyl compounds directly as a single-carbon synthon provided new highly efficient method for synthesis 2,3-disubstituted pyrroles in moderate to good yields with broad functional group compatibility.

Язык: Английский

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Synthesis of Pyrrole via Formal Cycloaddition of Allyl Ketone and Amine under Metal-Free Conditions

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(18), С. 12482 - 12490

Опубликована: Сен. 2, 2022

A new metal-free synthesis of pyrrole from allyl ketone and amine has been established. The reaction proceeds via an thiolative activation the C–C double bond with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by a nucleophilic ring-opening addition primary to generated episulfonium intermediate, then internal condensation aromatization. This mild procedure provides novel strategy construction substituted pyrroles through formal [4 + 1] cycloaddition reaction.

Язык: Английский

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Tetrasubstituted Imidazole Derivatives and Their Imidazolium: Photophysical Properties in Aggregate State and Application in Adenosine Detection

Materials Chemistry Frontiers, Год журнала: 2024, Номер 8(11), С. 2358 - 2366

Опубликована: Янв. 1, 2024

The anion–π + interaction induces tetraphenylimidazole salts to be AIE active by enhancing the spatial configuration. However, for diphenylphenanthroimidazole enhanced π–π stacking reduce fluorescence quantum yields.

Язык: Английский

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Asymmetric tetraphenyl-substituted butadienes with aggregation-induced emission characteristic: Synthesis, properties and applications

Dyes and Pigments, Год журнала: 2023, Номер 215, С. 111252 - 111252

Опубликована: Март 21, 2023

Язык: Английский

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