92647-87-5Relevant academic research and scientific papers
Double nucleophilic reaction of amines to the imidazole nucleus and selective synthesis of 5-aminoimidazoles
Kawasaki, Ikuo,Osaki, Tomohisa,Tsunoda, Kazuya,Watanabe, Emiko,Matsuyama, Makie,Sanai, Akiko,Khadeer, Abdul,Yamashita, Masayuki,Ohta, Shunsaku
, p. 6639 - 6648 (2007/10/03)
Reaction of 2-(1-chloro-2,2-dimethylpropyl)-1-methyl-1H-imidazole with an excess of N,N-dimethylamine at room temperature gave an abnormal adduct, trans-4,5-bis(dimethylamino)-1-methyl-2,2-dimethylpropyl-2-imidazoline, which was derived from a serial, double nucleophilic addition into the imidazole nucleus in 74% yield together with a normal SN product, 1-methyl-2-(1-dimethylamino-2,2-dimethylpropyl)-1H-imidazole in 15% yield. The former was easily converted to 1-methyl-5-(dimethylamino)-2-(2,2-dimethylpropyl) -1H-imidazole by only reflux in toluene in 90% yield. The scope, mechanism and limitation of these reactions are discussed.
