Syntheses, reactivity, and biological applications of coumarins

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Feb. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Language: Английский

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Organophotoelectrochemical silylation cyclization for the synthesis of silylated 3-CF₃-2-oxindoles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3585 - 3590

Published: Jan. 1, 2023

An organophotoelectrochemical approach for silylation cyclization of CF3-substituted N -arylacrylamides with organosilanes under transition-metal-free and oxidant-free conditions has been developed.

Language: Английский

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Chloride‐Promoted Photoelectrochemical C—H Silylation of Heteroarenes^†

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(22), P. 2963 - 2968

Published: June 24, 2023

Comprehensive Summary A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H 2 evolution has been developed. The depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated light‐induced homolytic cleavage Cl , in which was produced by electrochemical oxidation chloride. large number silylated heterocyclic molecules are rapidly constructed satisfactory yields without relying oxidants and metal reagents.

Language: Английский

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Copper‐Catalyzed Radical Silylarylation of Activated Alkenes: Preparation of β‐Silyl Amide‐Pharmaceutical Hybrids

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1325 - 1330

Published: Feb. 2, 2024

Abstract Copper‐catalyzed silylarylation of N ‐(arylsulfonyl)acrylamides via a tandem silyl radical addition/1,4‐aryl migration/desulfonylation sequence has been developed. This method employs silanes as the precursor and di‐ tert ‐butyl peroxide (DTBP) initiator. By using this cascade procedure, series β ‐silyl amide‐pharmaceutical hybrids which contain an α ‐all‐carbon quaternary stereocenter were facilely synthesized.

Language: Английский

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Electrochemical Decarboxylative Silylation of α,β-Unsaturated Carboxylic Acids

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4562 - 4566

Published: June 14, 2023

An electrochemical method for the decarboxylative silylation of α,β-unsaturated carboxylic acids was developed. A variety alkenylsilanes could be obtained in satisfactory yields and excellent selectivities under external oxidant- metal-free conditions. Mechanistic studies showed that formation silyl radical mediated by NHPI, which produces hydrogen atom transfer (HAT) reagent phthalimide N-oxyl (PINO) via multiple-site concerted proton-electron (MS-CPET).

Language: Английский

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HAT-Mediated Electrochemical C(sp²)–H Acylation of Quinolines with Alcohols

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7327 - 7331

Published: Oct. 5, 2023

Herein, an electrochemical hydrogen atom transfer (HAT) strategy for C(sp2)–H formylation of electron-deficient quinolines and isoquinolines is described. The cheap methanol acts as a formyl source with catalytic amount N-hydroxyphthalimide (NHPI) the catalyst. advantages this reaction are transition-metal-catalyst- chemical-oxidant-free conditions, protocol could also be applied to direct acetylation or propionylation quinolines.

Language: Английский

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Electrochemical synthesis of allenyl silanes and allenyl boronic esters

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: May 17, 2025

Allenyl silanes and boronates are pivotal building blocks in organic synthesis. Nevertheless, their synthesis requires the manipulation of transition metal or highly reactive species. Hence, development more sustainable protocol is sought after. Here we show electrochemical allenyl boronic esters. This catalyst-free method proceeds under mild reaction conditions. The for shows an excellent efficiency a good functional group tolerance. isolated yields (28 examples, 45-95% yields) without use catalyst A similar developed boronates, which obtained low to moderate (13 5-55% yields). Finally, mechanism based on oxidative generation silyl boryl radicals suggested access these classes allenes.

Language: Английский

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Electrochemical C–H silylation of azauracils with hydrosilanes

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 583, P. 115218 - 115218

Published: May 24, 2025

Language: Английский

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Electrochemical chlorination of least hindered tertiary and benzylic C(sp³)–H bonds

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(1), P. 507 - 512

Published: Dec. 1, 2023

Functionalization of C(sp 3 )–H bonds should greatly benefit the synthesis natural products and pharmaceuticals.

Language: Английский

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Acyl radicals generated from aldehydes with NHPI as electrocatalyst: aldehydes and alcohols as carbon-centered radical precursors

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4842 - 4848

Published: Jan. 1, 2024

We describe how N -hydroxyphthalimide (NHPI) promotes hydrogen atom transfer from aldehydes under electrochemical conditions. NHPI plays a multifunctional role, enabling the consideration of or alcohols as sp 3 -carbon centered radicals.

Language: Английский

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