A new convenient route for the synthesis of 4(5)-(ω-aminoalkyl)-1H-imidazoles

Article abstract of DOI:10.1002/recl.19931120208

A new route for the synthesis of 4(5)-(ω-aminoalkyl)-1H-imidazoles 1 on a preparative scale through C5 lithiation of a 1,2-diprotected imidazole is described.When the described 1,2-diprotected 5-lithio-imidazole is treated with a 1-chloro-ω-iodoalkane 5, selective substitution of the iodo group takes place.The chloro group of the resultant 1,2-diprotected 5-(ω-chloroalkyl)imidazole can be easily converted into an amino group, but obviously other functional groups can be introduced as well.Subsequent deprotection of the 5-substituted imidazole affords 4(5)-(ω-aminoalkyl)-1H-imidazoles 1, as precursors for a large range of histaminergic compounds, in good overall yields.