Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-a]pyridines DOI
Debojyoti Mukherjee, Indrajit Karmakar, Goutam Brahmachari

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12071 - 12084

Published: Aug. 15, 2024

We herein disclose a dual synthetic approach involving electrochemical and mechanochemical strategies for diversely functionalized 3-nitro-2-aryl-immidazo[1,2-a]pyridines. Both methods offer practical straightforward alternative route accessing this important class of biologically promising nitrogen-containing heterocycles. Significant advantages the newly developed include mild energy-efficient reaction conditions, avoidance transition metal catalysts, external heating additional oxidants, shorter times, good to excellent yields, broad substrate scope, gram-scale applicability, operational simplicity, eco-friendliness. Furthermore, application was extended by successfully reducing synthesized 3-nitro-2-aryl-immidazo[1,2-a]pyridines their corresponding amino derivatives.

Language: Английский

Electrochemical C3-methylthiolation of imidazopyridines with dimethyl sulfoxide DOI

Zhaoyue Feng,

Y. C. Fan,

Congcong Qiang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3517 - 3521

Published: Jan. 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.

Language: Английский

Citations

8
Metal-Free Synthesis of Trifluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines via Dehydrative Coupling of Imidazo[1,2-a]pyridines with Trifluoroacetaldehyde DOI
Xiaohua Guo, Kai Yang, Zhaowen Liu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(11), P. 1756 - 1764

Published: Jan. 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.

Language: Английский

Citations

4
Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications DOI Creative Commons
Giorgio Volpi, Enzo Laurenti, Roberto Rabezzana

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2668 - 2668

Published: June 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.

Language: Английский

Citations

4
Recent Advances in Visible Light-Induced C-H Functionalization of Imidazo[1,2-a]pyridines DOI Creative Commons
Juanjuan Gao,

Xinlei Fu,

Kai Yang

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 607 - 607

Published: Jan. 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.

Language: Английский

Citations

0
HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature DOI
Srinivasarao Yaragorla,

Aayesha Shaik,

Dandugula Sneha Latha

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Citations

0
Synthesis of 5-(Trifluoromethyl)-2,3-dihydrofurans through N-Alkylation of Azoles Using Brominated Enones DOI
Genilson S. Pereira, Mateus Mittersteiner, Nilo Zanatta

et al.

Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
C(sp2)‐H Imination of Imidazo[1,2‐a]pyridines: A Catalyst‐Free, Multicomponent Approach DOI

Yadavalli Subba Rao,

Doma Arun,

Nagaraju Devunuri

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(19)

Published: March 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.

Language: Английский

Citations

2
Photoredox-Cobaloxime Catalysis for Selective Oxidative Dehydrogenative [4+2] Annulation of Imidazo-Fused Heterocycles with Alkenes DOI
Ailong Shao, Yuanyuan Li,

Yuxue Ding

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2529 - 2534

Published: March 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.

Language: Английский

Citations

2
Visible light-mediated copper catalyzed regioselective diamination of terminal alkynes at room temperature: a facile synthesis of substituted imidazo[1,2-α]pyridines DOI
Vaibhav Pramod Charpe, Mahima Gupta, Kuo Chu Hwang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(3), P. 1329 - 1337

Published: Dec. 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.

Language: Английский

Citations

5
Synthesis of 2‐Aminopyridine Derivatives via a Tandem CuAAC/Ring‐Cleavage/[4+2]‐Cycloaddition/Rearrangement Reaction Sequence DOI
Weiguang Yang,

Guanrong Li,

Danyang Luo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3689 - 3694

Published: June 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.

Language: Английский

Citations

1