Electrochemical C3-methylthiolation of imidazopyridines with dimethyl sulfoxide

Green Chemistry, Год журнала: 2024, Номер 26(6), С. 3517 - 3521

Опубликована: Янв. 1, 2024

An electrochemical C-3 methylthiolation reaction of imidazo[1,2- a ]pyridines was achieved. The method used DMSO as both the methylthiolating reagent and solvent KI hydrogen atom transfer supporting electrolyte.

Язык: Английский

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Recent Advances in Visible Light-Induced C-H Functionalization of Imidazo[1,2-a]pyridines

Molecules, Год журнала: 2025, Номер 30(3), С. 607 - 607

Опубликована: Янв. 30, 2025

The imidazo[1,2-a]pyridine skeleton is widely present in many natural products and pharmaceutical agents. Due to its impressive significant biological activities, such as analgesic, anti-tumor, antiosteoporosis, anxiolytic properties, the derivatization of has attracted widespread attention from chemists. In recent years, progress been made imidazo[1,2-a]pyridines through direct C-H functionalization, especially visible light induction. This review highlights advances light-induced functionalization during past ten some reaction mechanisms are also discussed.

Язык: Английский

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Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications

Molecules, Год журнала: 2024, Номер 29(11), С. 2668 - 2668

Опубликована: Июнь 5, 2024

In recent years, there has been increasing attention focused on various products belonging to the imidazopyridine family; this class of heterocyclic compounds shows unique chemical structure, versatile optical properties, and diverse biological attributes. The broad family imidazopyridines encompasses different heterocycles, each with its own specific properties distinct characteristics, making all them promising for application fields. general, useful category aromatic heterocycles holds significant promise across research domains, spanning from material science pharmaceuticals. cores exhibit such as serving emitters in imaging, ligands transition metals, showing reversible electrochemical demonstrating activity. Recently, numerous noteworthy advancements have emerged technological fields, including optoelectronic devices, sensors, energy conversion, medical applications, shining imaging microscopy. This review intends provide a state-of-the-art overview framework 1955 present day, unveiling aspects applications. extensive literature survey may guide chemists researchers quest novel enhanced efficiency uses.

Язык: Английский

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Metal-Free Synthesis of Trifluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines via Dehydrative Coupling of Imidazo[1,2-a]pyridines with Trifluoroacetaldehyde

Synthesis, Год журнала: 2024, Номер 56(11), С. 1756 - 1764

Опубликована: Янв. 25, 2024

Abstract A facile and efficient method for the synthesis of trifluoromethylated carbinols has been developed from imidazo[1,2-a]pyridines trifluoroacetaldehyde. The direct C(sp2)–H hydroxytrifluoromethylation is successfully implemented at room temperature using HFIP as solvent through dehydrative cross-coupling process, which displays a broad substrate scope functional group tolerance. Furthermore, gram-scale synthetic transformation experiments have also demonstrated, indicate its potential applicable values in organic synthesis. This green protocol features operational simplicity, atom economy, mild reaction conditions (e.g., temperature, transition-metal- oxidant-free, without inert gas protection), wide scope, excellent practicality.

Язык: Английский

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Photoredox-Cobaloxime Catalysis for Selective Oxidative Dehydrogenative [4+2] Annulation of Imidazo-Fused Heterocycles with Alkenes

Organic Letters, Год журнала: 2024, Номер 26(13), С. 2529 - 2534

Опубликована: Март 21, 2024

A selective oxidative [4+2] annulation of alkenes with imidazo-fused heterocycles has been developed by using the synergistic combination photoredox and cobaloxime catalysts. It allows facile access to various imidazole-fused polyaromatic scaffolds accompanied H2 evolution. This protocol features high regioselectivity as well a broad substrate scope. Detailed mechanistic studies indicate that twice electron/H transfer processes facilitated this catalytic system achieve π-extension alkenes.

Язык: Английский

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HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 25, 2025

Herein, we report an efficient synthetic protocol for the Friedel–Crafts reaction of imidazo[1,2-a]pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In method, HFIP, besides offering hydrogen bonding alcohol, also stabilizes resultant carbocation, thus forming product. This method enables straightforward synthesis 1,3-enynes. The current offers a large substrate diversity good to excellent yields. We demonstrated gram-scale modifications.

Язык: Английский

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Synthesis of 5-(Trifluoromethyl)-2,3-dihydrofurans through N-Alkylation of Azoles Using Brominated Enones

Synthesis, Год журнала: 2025, Номер unknown

Опубликована: Апрель 7, 2025

Abstract We herein present a chemo- and regioselective methodology for the N-alkylation/arylation of azoles (imidazoles, pyrazoles, triazoles) using 5-bromo-1,1,1-trifluoro-4-alkoxypent-3-en-2-ones (brominated enones) as precursors, in order to selectively obtain N-alkylated containing disubstituted furans or dihydrofurans. The key reaction steps are 1,4-conjugated addition followed by nucleophilic substitution (each promoted different nitrogen atom azole), which furnish corresponding 2,5-disubstituted dihydrofurans (24 examples, yields 37–97%). limitations explored it is found that when 2-chlorobenzimidazole used dinucleophile, 5-trifluoromethyl-3-substituted obtained (three 57–67%). selectivity reactions determined through NMR analysis (including two-dimensional techniques 15N nucleus) single-crystal X-ray analysis.

Язык: Английский

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C(sp²)‐H Imination of Imidazo[1,2‐a]pyridines: A Catalyst‐Free, Multicomponent Approach

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(19)

Опубликована: Март 5, 2024

Abstract We report here a catalyst‐free, (sp 2 )C−H imination reaction of in‐situ formed imidazo[1,2‐ ]pyridines and α‐iminoketones. This one‐pot, multicomponent, atom economic is performed at moderate to room temperature without the need for any catalyst inert conditions. The showed good substrate tolerance with appreciable yields. Gram‐scale synthesis post‐synthetic modifications obtain 1,2‐diketones are also described.

Язык: Английский

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Visible light-mediated copper catalyzed regioselective diamination of terminal alkynes at room temperature: a facile synthesis of substituted imidazo[1,2-α]pyridines

Green Chemistry, Год журнала: 2023, Номер 26(3), С. 1329 - 1337

Опубликована: Дек. 21, 2023

We have developed a protocol for the regioselective synthesis of substituted imidazo[1,2-α]pyridines at room temperature using low-energy visible light, inexpensive CuCl as catalyst, readily available starting materials, mild reaction conditions, and O 2 green oxidant.

Язык: Английский

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Synthesis of 2‐Aminopyridine Derivatives via a Tandem CuAAC/Ring‐Cleavage/[4+2]‐Cycloaddition/Rearrangement Reaction Sequence

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3689 - 3694

Опубликована: Июнь 22, 2024

Abstract 2 H ‐Azirines are an important class of small‐ring heterocycle that have been employed as versatile synthetic building blocks. Herein, a one‐pot CuAAC/ring‐cleavage/[4+2]‐cycloaddition/rearrangement reaction sequence involving terminal ynones, sulfonyl azides and ‐azirines is reported leads to 2‐aminopyridine derivatives. In the first step, highly reactive N ‐sulfonyl α ‐acylketenimines generated, via CuAAC/ring‐cleavage process, from ynones these undergo inverse electron‐demand Diels–Alder cycloaddition reactions with form (isolable) 1,3‐oxazines themselves base‐promoted ring‐cleavage rearrangement afford title compounds.

Язык: Английский

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