Recent Developments in the Photochemical Synthesis of Functionalized Imidazopyridines

Molecules, Год журнала: 2022, Номер 27(11), С. 3461 - 3461

Опубликована: Май 27, 2022

Imidazopyridines constitute one of the most important scaffolds in medicinal chemistry, as their skeleton could be found a myriad biologically active molecules. Although numerous strategies were elaborated for imidazopyridine preparation 2010s, novel eco-compatible synthetic approaches have emerged, conscious climate change concerns. In this framework, photochemical methods been promoted to conceive heterocyclic motif over last decade. This review covers recently published works on synthesizing highly functionalized imidazopyridines by light induction.

Язык: Английский

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Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp²)–H Bond Selenylation of Imidazo[2,1-b]thiazole and Related Structures

ACS Omega, Год журнала: 2023, Номер 8(42), С. 39535 - 39545

Опубликована: Окт. 12, 2023

Herein, we describe a urea hydrogen peroxide-mediated sustainable protocol for the synthesis of selenylated imidazo[2,1-b]thiazole by using half molar equivalent diorganyl diselenides in ethyl lactate as greener solvent. The reaction features high yields, easy performance on gram scale, metal-free conditions, well applicability to imidazopyridine and imidazopyrimidine.

Язык: Английский

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Silver-catalyzed direct selanylation of indoles: synthesis and mechanistic insights

RSC Advances, Год журнала: 2023, Номер 13(2), С. 914 - 925

Опубликована: Янв. 1, 2023

Herein we describe the Ag(i)-catalyzed direct selanylation of indoles with diorganoyl diselenides. The reaction gave 3-selanylindoles high regioselectivity and also allowed access to 2-selanylindoles when C3 position indole ring was blocked

Язык: Английский

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Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics

Molecules, Год журнала: 2021, Номер 26(15), С. 4446 - 4446

Опубликована: Июль 23, 2021

Herein, we describe a simple and efficient route to access aniline-derived diselenides evaluate their antioxidant/GPx-mimetic properties. The were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These present GPx-mimetic properties, showing better antioxidant activity than standard compounds, ebselen diphenyl diselenide. DFT analysis demonstrated that electronic properties of substituents determine charge delocalization partial on selenium, which correlate with catalytic performances. amino group concurs stabilization selenolate intermediate through hydrogen bond selenium.

Язык: Английский

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Oxone® Mediated Regioselective C(sp²)−H Selenylation and Thiocyanation of Pyrazolo[1,5‐a]pyrimidines at Room Temperature

ChemistrySelect, Год журнала: 2024, Номер 9(1)

Опубликована: Янв. 2, 2024

Abstract A mild Oxone® mediated reaction for direct regioselective C−H selenylation and thiocyanation of pyrazolo[1,5‐ a ]pyrimidines is established at ambient temperature. This practical efficient methodology employs as user friendly, green, non‐toxic cheap reagent to facilitate room The present method offers high regioselectivity, broad substrate scope, conditions excellent yields. Further, this eco‐friendly approach could easily be extended other heterocycles. Mechanistic studies indicate that the occurs through electrophilic substitution mechanism via generation an chalcogen species.

Язык: Английский

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A sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155504 - 155504

Опубликована: Фев. 1, 2025

Язык: Английский

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Catalyst- and metal-free C(sp2)–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature

Scientific Reports, Год журнала: 2023, Номер 13(1)

Опубликована: Авг. 31, 2023

In this paper, we report an eco-friendly approach for the C(sp2)-H bond selenylation of imidazopyridines and other N-heteroarenes as well simple arenes at ambient temperature. This new protocol consists reaction between (N-hetero)-arenes diorganyl-diselenides trichloroisocyanuric acid (TCCA)-ethanol reagent system. a short time, desired selenylated products were obtained regioselectively in good yields, with tolerance wide range functional groups.

Язык: Английский

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Lighting Up the Organochalcogen Synthesis: A Concise Update of Recent Photocatalyzed Approaches

Catalysts, Год журнала: 2023, Номер 13(3), С. 520 - 520

Опубликована: Март 3, 2023

This review describes the recent advances in photocatalyzed reactions to form new carbon–sulfur and carbon–selenium bonds. With a total of 136 references, which 81 articles are presented, authors introduce five sections an updated picture state art light-promoted synthesis organochalcogen compounds (from 2019 present). The sulfides by direct sulfenylation C–C π-bonds; sulfones; activation Csp2–N bond formation Csp2–S bonds; thiol ester, thioether thioacetal; organoselenium discussed, with detailed reaction conditions selected examples for each protocol.

Язык: Английский

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Recent Advances in the Use of Diorganyl Diselenides as Versatile Catalysts

Molecules, Год журнала: 2023, Номер 28(18), С. 6614 - 6614

Опубликована: Сен. 14, 2023

The importance of organoselenium compounds has been increasing in synthetic chemistry. These reagents are well-known as electrophiles and nucleophiles many organic transformations, recent years, their functionality catalysts also largely explored. interest organoselenium-based is due to high efficacy, mild reaction conditions, strong functional compatibility, great selectivity. Allied catalysts, the use inorganic oxidants that act by regenerating catalytic species for pathway common. Here, we provide a comprehensive review last five years transformations promoted diorganyl diselenide selenium-based catalyst. This report divided into four sections: (1) cyclisation reactions, (2) addition reactions oxidative functionalisation, (3) oxidation reduction (4) involving phosphorus-containing starting materials.

Язык: Английский

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Electrochemical Regioselective C(sp2)-H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross Coupling at Room Temperature

Опубликована: Апрель 9, 2024

In this report, we disclose an electrochemical approach for the C(sp2)-H chalcogenation of pyrazolo[1,5-a]pyrimidines at room temperature via radical cross-coupling reaction. The reaction takes place within undivided cell employing graphite electrodes, with TBABF4 acting as supporting electrolyte. This technique offers a rapid, oxidant-free, and environmentally conscious protocol achieving regioselective specifically C3 position pyrazolo[1,5-a]pyrimidines. Furthermore, procedure uses only 0.5 equivalents diaryl chalcogenides which underscores atom economy protocol. Key attributes methodology include mild conditions, short time, utilization cost-effective electrode materials, reliable achievement yields ranging from good to excellent friendly conditions. Cyclic voltammetry studies quenching experiments suggest pathway mechanism.

Язык: Английский

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