Studies on the Radziszewski Reaction—Synthesis and Characterization of New Imidazole Derivatives

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Abstract
Two new long-chain N-alkyl imidazole derivatives, 2-(1-octadecyl-imidazol-2-yl)pyridine and 2-(furan-2-yl)-1-(octadecane-1-yl)-1H-imidazole, were synthesized via the Radziszewski reaction followed by N-alkylation. This is the first report of furan-imidazole obtained by this route using furfuraldehyde as a renewable biomass-derived precursor. FTIR, 1D/2D solution NMR, and HRMS confirmed the structural elucidation, while XRD and solid-state 13C CPMAS NMR corroborated the crystal structures of the precursors. Notably, previously misassigned 1H and 13C chemical shifts reported in the literature for pyridine and furan-imidazole precursors were corrected. Furthermore, 13C CPMAS NMR spectra of those precursors are reported here for the first time. These findings expand the scope of the Radziszewski reaction and provide new insights into the structural characterization of imidazole-based systems.

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