HARNESSING FERROCENECARBOXALDEHYDE IN MULTICOMPONENT REACTIONS FOR THE SYNTHESIS OF BIOACTIVE HETEROCYCLIC FERROCENES
DOI:
https://doi.org/10.15421/jchemtech.v33i3.336225Keywords:
condensation, heterocycles, ferrocenecarboxaldehyde, multicomponent reactions (MCR)Abstract
Multicomponent reactions (MCRs) offer a sustainable and efficient approach to synthesizing complex molecular scaffolds, aligning with green chemistry principles. This study explores the underexploited synthetic potential of ferrocenecarboxaldehyde in MCRs to construct heterocyclic ferrocene derivatives, motivated by their promising bioactivity in medicinal chemistry, potential in materials science, organic synthesis and environmental testing. Through reactions such as the Biginelli condensation, photocatalyzed synthesis, and tandem processes involving malononitrile, ketosulfone, and hydrazines, a diverse array of heterocyclic compounds was synthesized. Structural confirmation was achieved using ¹H and ¹³C NMR, GCMS, and LCMS, despite challenges with solubility and side reactions like decarboxylation and Cannizzaro processes. Successful syntheses included pyrimidine, pyridine and benzimidazole derivatives, with yields ranging from 5 % to 69 %. Several procedures were employed that avoided the need for column chromatography in target product isolation. These findings highlight ferrocenecarboxaldehyde versatility in generating bioactive heterocycles, paving the way for further exploration in drug discovery and materials science.
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