Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride: facile formation of 2,4,5- triphenylimidazoline derivatives

作者: Jiro Tsuji , Kiyomi Sakai , Hisao Nemoto , Hideo Nagashima

DOI: 10.1016/0304-5102(83)80116-3

关键词: Imidazoline receptorImidazoleCopper catalyzedDehydrogenationOrganic chemistryCarbon tetrachlorideCopperChemistryBenzylamineMedicinal chemistryCatalysis

摘要: Abstract Iron and copper salts catalyzed the reaction of benzylamine with CCl 4 to give a mixture 2,4,5-triphenylimidazole (1), 1-benzyl-2,4,5-triphenylimidazole (2), 2,4,5-triphenylimidazoline (3), 1-benzyl-2,4,5-triphenylimidazoline (4) in high yields. The imidazoline was obtained as main product. imidazole derivatives were also formed by iron-catalyzed benzylidenebenzylamine (8) or dibenzylamine (5) . slowly underwent debenzylation dehydrogenation aid iron catalyst 1 2. From these results, mechanism involving formation 5 8, subsequent oxidative dimerization 8 form 4, further conversion 1, 2, 3 is proposed.

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