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2004
Imidazole derivatives
R 0190
Double Nucleophilic Reaction of Amines to the Imidazole Nucleus and Selective
of 5-Aminoimidazoles. — A novel, stereoselective double nucleophilic
47- 115 Synthesis
addition of amines into the imidazole nucleus affords dearomatized bisaminoimidazolines (V) together with a normal SN product. The influence of steric hindrance and the
kind of nucleophile are investigated. Dearomatizing reactions are only found with
amines. Other nucleophiles such as thiol, alcohol and phenol under the same conditions
only give SN products. Conversion of bisaminoimidazolines (V) into 5-aminoimidazoles (VIII) is effected by reflux in toluene. — (KAWASAKI, I.; OSAKI, T.;
TSUNODA, K.; WATANABE, E.; MATSUYAMA, M.; SANAI, A.; KHADEER, A.;
YAMASHITA, M.; OHTA*, S.; Tetrahedron 60 (2004) 31, 6639-6648; Kyoto Pharm.
Univ., Misasagi, Yamashina, Kyoto 607, Japan; Eng.) — Bartels
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