Photoinduced, Direct C(sp²)−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y

Abstract

Herein, a greener approach to the eosin Y‐Na2 catalyzed, C(sp2)−H bond azo coupling of imidazoheteroarene with aryl diazonium salts is described, under acid free conditions. This direct photoredox process resulted in the corresponding azo products in good to excellent yields. Besides, this new approach could also be applicable to anilines, which is a poorly reactive substrate by other methods. The main features of this reaction are that it provides high yields and is gram‐scalable and applicable to biologically relevant imidazoheteroarenes and ‐anilines.

IP-Se-06, a Selenylated Imidazo[1,2-a]pyridine, Modulates Intracellular Redox State and Causes Akt/mTOR/HIF-1α and MAPK Signaling Inhibition, Promoting Antiproliferative Effect and Apoptosis in Glioblastoma Cells

“…Compounds containing the imidazo[1,2- a ]pyridines (IPs) heterocycle system have been largely used in medicinal chemistry and drug development [ 10 ]. These compounds possess a wide spectrum of biological activity and pharmacological properties by binding on different targets [ 11 ].…”

Selenylated-oxadiazoles as promising DNA intercalators: Synthesis, electronic structure, DNA interaction and cleavage

“…As part of our continuing research interest in the synthesis of biologically relevant organoselenium compounds [36][37][38] and material chemistry [39][40][41][42], herein we report the synthesis of selenylated-ODZ, their characterization, DNA interaction, and plasmid DNA cleavage activity. Furthermore, the photophysical, thermal and electrochemical properties of the selenylated products were explored and were also supported by theoretical studies.…”

Versatile Electrochemical Synthesis of Selenylbenzo[b]Furan Derivatives Through the Cyclization of 2-Alkynylphenols

“…Thus, in connection with our continuing interest in designing and developing eco-friendly processes ( Godoi et al, 2013 ; Matzkeit et al, 2018 ; Peterle et al, 2018 ; Scheide et al, 2020a ; Neto et al, 2020 ; Saba et al, 2020 ; Franco et al, 2021 ) and electrochemical selenylation reactions ( Meirinho et al, 2019 ; Lazzaris et al, 2021 ; Scheide et al, 2021 ), we report the synthesis of selenylbenzo[ b ]furan derivatives through an electrochemical oxidative intramolecular cyclization reaction between 2-alkynylphenol derivatives and different diorganyl diselenides. This sustainable approach operates in shorter reaction time, providing the selenylated products in good to excellent yields.…”