Chitosan-EDTA-Cellulose network as a green, recyclable and multifunctional biopolymeric organocatalyst for the one-pot synthesis of 2-amino-4H-pyran derivatives

Scientific Reports, Journal Year: 2022, Volume and Issue: 12(1)

Published: May 23, 2022

Abstract In this research, cellulose grafted to chitosan by EDTA (Cs-EDTA-Cell) bio-based material is reported and characterized a series of various methods techniques such as FTIR, DRS-UV–Vis, TGA, FESEM, XRD EDX analysis. fact, the Cs-EDTA-Cell network more thermally stable than pristine or chitosan. There plenty both acidic basic sites on surface biodegradable network, multifunctional organocatalyst, proceed three-component synthesis 2-amino-4 H -pyran derivatives at room temperature in EtOH. The nanocatalyst can be easily recovered from reaction mixture using filtration reused for least five times without significant decrease its catalytic activity. general, heterogeneous catalyst, demonstrated excellent activity an environmentally-benign solvent afford desired products short required simple experimental work-up procedure compared many protocols similar systems.

Language: Английский

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Copper-Catalyzed Selective Electron Transfer Enables Switchable Divergent Synthesis of 3-Functionalized Oxindoles

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(5), P. 3085 - 3092

Published: Feb. 16, 2023

Oxidative rearrangement of 3-substituted indoles is a fundamental organic transformation for the synthesis 2-oxindole scaffolds. However, this time-consuming and complex task produces single type product via two-electron oxidation using stoichiometric chemical oxidants. Herein, we report unified efficient copper-catalyzed selective single-electron transfer strategy three reactions air (O2) as terminal oxidant, providing streamlined practical synthetic approach to access 3-hydroxyl-, 3-alkoxyl-, 3-hygrogenous-2-oxindoles 3-radical-2-hydroxyl indoline intermediate. This copper catalysis protocol demonstrates high chemoselectivity, good functional group tolerance, broad application potential in modular biologically 3-functionalized oxindole derivatives.

Language: Английский

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Recent Advances on Direct Functionalization of Indoles in Aqueous Media

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(3)

Published: Feb. 1, 2023

Abstract Indoles and their derivatives have dominated a significant proportion of nitrogen‐containing heterocyclic compounds play an essential role in synthetic medicinal chemistry, pesticides, advanced materials. Compared with conventional strategies, direct functionalization indoles provides straightforward access to construct diverse indole scaffolds. As we enter era emphasizing green sustainable utilizing environment‐friendly solvents represented by water demonstrates great potential synthesizing valuable derivatives. This review aims depict the critical aspects aqueous‐mediated over past decade discusses future challenges prospects this fast‐growing field. For convenience readers, is classified into three parts according bonding modes (C−C, C−N, C−S bonds), which focus on diversity derivatives, prominent chemical process, types catalyst systems mechanisms. We hope can promote development discovery novel practical organic methods aqueous phase.

Language: Английский

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Magnetic decorated 5-sulfosalicylic acid grafted to chitosan: A solid acid organocatalyst for green synthesis of quinazoline derivatives

Carbohydrate Polymer Technologies and Applications, Journal Year: 2024, Volume and Issue: 7, P. 100420 - 100420

Published: Jan. 3, 2024

In this research, a new magnetically decorated multifunctional solid acid was designed and prepared conveniently by grafting of 5-sulfosalicylic (SSA) onto the chitosan (CS) backbone using toluene-2,4-diisocyanate (TDI) linker for first time. The obtained magnetic biopolymeric nanomaterial, CS-TDI-SSA-Fe3O4, properly characterized spectroscopic, microscopic, or analytical methods including FT-IR, EDX, XRD, BET, FESEM, TGA, VSM. supramolecular CS-TDI-SSA-Fe3O4 nanocomposite investigated, as heterogeneous organocatalyst, to promote three-component synthesis 2,3-dihydroquinazoline-4(1H)-one derivatives under green conditions. acidic nanocatalyst demonstrated highly efficient activity wide range quinazoline derivatives, an important pharmaceutical scaffold, through multicomponent strategy. reaction proceeds very well in presence EtOH afford corresponding (DHQ) high excellent yields. key advantages present protocol are use novel, renewable, biopolymeric, biodegradable simple procedure preparation hybrid material. Furthermore, catalyst can be used at least five times DHQ with slight decrease its catalytic activity.

Language: Английский

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The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1213 - 1220

Published: May 27, 2024

Considering early-stage drug discovery programs, the Ugi four-component reaction is a valuable, flexible, and pivotal tool, facilitating creation of two new amide bonds in one-pot fashion to effectively yield desired α-aminoacylamides. Here, we highlight reputation this approach access number scaffold diversity library isatin-based α-acetamide carboxamide oxindole hybrids, promising anticancer agents, mild fast sustainable process. The was tested against six human solid tumor cell lines, among them, non-small lung carcinoma, cervical adenocarcinoma, breast cancer colon adenocarcinoma. most potent compounds 8d , 8h 8k showed GI 50 values range 1–10 μM.

Language: Английский

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A Diversity‐Oriented Multicomponent Approach to Novel Fused Nitrogen Heterocycles Using 6‐Aminoindazole

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(14)

Published: April 1, 2025

Abstract We present a novel, efficient, eco‐friendly sonochemical strategy for the synthesis of fused nitrogen heterocycles via Brønsted acid‐promoted, one‐pot multicomponent reactions (MCRs). This method involves rapid assembly 6‐aminoindazole, aryl aldehydes, and 1,3‐cyclodione derivatives (barbituric acid, dimedone, 1,3‐dimethyl barbituric acid) under mild identical reaction conditions. The approach delivers diverse range highly functionalized heterocyclic frameworks, including 11‐phenyl‐1,6,7,11‐tetrahydro‐8 H ‐pyrazolo[3,4‐ f ]pyrimido[4,5‐ b ]quinoline‐8,10(9 )‐dione, 8,8‐dimethyl‐11‐phenyl‐1,6,7,8,9,11‐hexahydro‐10 ]acridin‐10‐one, 7,9‐diphenyl‐1,6,7,9‐tetrahydro‐2′ ‐spiro[pyrazolo[3,4‐ ]quinoline‐8,5′‐pyrimidine]‐2′,4′,6′(1′ ,3′ )‐trione derivatives. molecular structures these compounds were unambiguously confirmed through 1H‐NMR, 13C‐NMR single‐crystal X‐ray diffraction (SC‐XRD) analysis. Additionally, control experiments provided valuable mechanistic insights into pathway. protocol stands out its efficiency, high yields, broad functional group tolerance, making it versatile tool diversity‐oriented in modern chemistry.

Language: Английский

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Access to chiral sulfones with an all-carbon quaternary stereocenter from sulfur dioxide

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4275 - 4283

Published: Jan. 1, 2024

A copper-catalyzed enantioselective four-component reaction via the insertion of sulfur dioxide toward synthesis chiral sulfones bearing an all-carbon quaternary stereocenter at β position is reported.

Language: Английский

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Ugi Reaction Synthesis of Oxindole–Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors

ACS Medicinal Chemistry Letters, Journal Year: 2021, Volume and Issue: 12(11), P. 1718 - 1725

Published: July 23, 2021

Molecular hybridization is a valuable approach in drug discovery. Combining it with multicomponent reactions highly desirable, since structurally diverse libraries can be attained efficiently an eco-friendly manner. In this work, isatin used as the key building block for Ugi 4-center 3-component reaction synthesis of oxindole–lactam hybrids, under catalyst-free conditions. The resulting oxindole−β-lactam and oxindole−γ-lactam hybrids were evaluated their potential to inhibit relevant central nervous system targets, namely cholinesterases monoamine oxidases. Druglikeness evaluation was also performed, compounds 4eca 5dab exhibited great selective butyrylcholinesterase inhibitors, at low micromolar range, interesting predictive pharmacokinetic profile. Our findings herein reported suggest new agents treatment Alzheimer's disease.

Language: Английский

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Substrate‐Controlled Regioselectivity Switch in a Three‐Component 1,3‐Dipolar Cycloaddition Reaction to Access 3,3′‐Pyrrolidinyl‐Spirooxindoles Derivatives

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(12), P. 2047 - 2052

Published: May 12, 2022

Abstract The additive‐free 1,3‐dipolar cycloaddition reaction of isatin‐derived azomethine ylides with α‐cyano‐α,β‐unsaturated compounds was developed, which enabled diversity‐oriented synthesis a series novel and structurally complex 3,3′‐pyrrolidinyl‐spirooxindoles derivatives containing four contiguous two quaternary stereogenic centers in high yields (up to 92%) excellent diastereoselectivities >25:1 dr). displays switchable regioselectivity depending on the steric effect substrates. magnified image

Language: Английский

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Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]

RSC Advances, Journal Year: 2023, Volume and Issue: 13(19), P. 13206 - 13212

Published: Jan. 1, 2023

A simple and efficient methodology for the one-pot synthesis of 3,3′-disubstituted oxindoles spiro[2- H -pyran-3,4′-indoline] featuring an all-carbon quaternary center has been demonstrated through l -proline catalysed three-component reaction.

Language: Английский

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