SYNTHESIS AND APPLICATION OF IMIDAZOLE DERIVATIVES - INTRODUCTION OF CARBOGENIC SUBSTITUENTS INTO THE 5-POSITION OF 1-METHYL-1H-IMIDAZOLE

被引：32
|
作者：
OHTA, S [1 ]
YAMAMOTO, T [1 ]
KAWASAKI, I [1 ]
YAMASHITA, M [1 ]
KATSUMA, H [1 ]
NASAKO, R [1 ]
KOBAYASHI, K [1 ]
OGAWA, K [1 ]
机构：
[1] TAIHO PHARMACEUT CO LTD, MED RES CTR, SAITAMA 357, JAPAN
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 10期
关键词：
LITHIATION; 1-METHYL-1H-IMIDAZOLE; X-RAY CRYSTALLOGRAPHY; LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE; 1-METHYL-2-PHENYLTHIO-1H-IMIDAZOLE; CARBANION; ELECTROPHILE; DESULFURIZATION;
D O I：
10.1248/cpb.40.2681
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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 H-1-NMR spectroscopy and X-ray crystallography. The phenylthio group of the 5-substituted compounds could be easily removed by treatment with Raney-nickel.
引用
收藏
页码：2681 / 2685
页数：5
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