N-Arylation of ferrocenyl 2,4-thiazolidinedione conjugatesviaa copper-catalysed Chan–Lam cross coupling reaction with aryl boronic acids and their optoelectronic properties

Abstract

Copper catalysed Chan–Lam N-arylation of ferrocenyl 2,4-thiazolidinedione conjugates is described.

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

“…Ferrocenyl 2,4‐thiazolidinediones 273 undergo N ‐arylation through coupling with different arylboronic acids 274 a – i using catalytic copper(II) acetate with triethylamine (Scheme 92). These compounds were tested for α‐glucosidase inhibition, compound 275 k has shown the highest inhibitory activity with IC 50 of 0.61 mg/ml [301] …”

“…These compounds were tested for α-glucosidase inhibition, compound 275 k has shown the highest inhibitory activity with IC 50 of 0.61 mg/ml. [301] N-Arylation is also investigated on 5-arylidene-2,4-thiazolidinediones 276 a-g by reacting with diaryliodonium tetrafluoroborates 277 a-c using ionic liquid [bmim]PF 6 in presence of potassium hydroxide to provide 3-aryl-5-arylidene-2,4-thiazolidinediones 278 a-j (Scheme 93). [302]…”

1,2,3‐Triazole derivatives of 3‐ferrocenylidene‐2‐oxindole: Synthesis, characterization, electrochemical and antimicrobial evaluation

“…Ferrocifens, hydroxyferrocifens and the ferrocene analogue of anti‐androgen, nilutamide, are some of the well‐known ferrocene derivatives that exhibit significant cytotoxicity. The ferrocene analogue of the antimalarial drug chloroquine, ferroquine, has also been studied extensively . These examples have provided impetus for the study of different types of ferrocene conjugates for biological applications …”

“…Structural motifs containing ferrocene‐triazoles and carbohydrate‐triazoles are known for their cytotoxicity and antimicrobial activities . Recently, our group has also reported on the biological properties of imidazolinones‐ and thiazolidinediones‐linked ferrocene derivatives . In continuation of these studies, herein, we describe the synthesis, electrochemical as well as antimicrobial activity of a series of different ferrocenyl triazole conjugates linked via oxindole moiety.…”

N‐Arylation of Fluoroalkylamine and Trifluoroacetamide through Cu–Catalysis

“…Undoubtedly, the development of efficient strategies for direct installation of fluoroalkyl/fluoroacetyl group is highly desirable. Recently, Hu et.al reported the synthesis of N‐fluoroalkylated aryl by Cu‐mediated Chan‐Lam‐Evans coupling reaction of aryl boronic acids with fluoroalkylamines . However, the reaction employed a high temperature (80°C) and only worked for fluoroalkylamine.…”