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

Shunsaku OHTA; Tetsuya YAMAMOTO; Ikuo KAWASAKI; Masayuki YAMASHITA; Hideo KATSUMA; Rieko Nasako; Kazuhiro KOBAYASHI; Kazuo OGAWA

doi:10.1248/cpb.40.2681

Shunsaku OHTA, Tetsuya YAMAMOTO, Ikuo KAWASAKI, Masayuki YAMASHITA, Hideo KATSUMA, Rieko Nasako, Kazuhiro KOBAYASHI, Kazuo OGAWA

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Keywords: lithiation, 1-methyl-1H-imidazole, X-ray crystallography, lithium 2, 2, 6, 6-tetramethylpiperidide, 1-methyl-2-phenylthio-1H-imidazole, carbanion, electrophile, desulfurization

JOURNAL FREE ACCESS

1992 Volume 40 Issue 10 Pages 2681-2685

DOI https://doi.org/10.1248/cpb.40.2681

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Abstract

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.

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