Synthesis and Application of Imidazole Derivatives. Introduction of Carbogenic Substituents into the 5-Position of 1-Methyl-1H-imidazole.

The 5-position of 1-methyl-2-phenylthio-1H-imidazole (12a) was lithiated by lithium 2, 2, 6, 6-tetramethylpiperidide, and the produced carbanion was reacted with various electrophiles to give the corresponding 5-substituted derivatives in good yields. The reaction position was confirmed by 1H-NMR spectroscopy and X-ray crystallography. The phenylthio group of the 5-substituted compounds could be easily removed by treatment with Raney-nickel.