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

✍ Scribed by Roeland C. Vollinga; Wiro M. P. B. Menge; Hendrik Timmerman

• Book ID: 104589493
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 293 KB
• Volume: 112
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19931120208

✦ Synopsis

Abstract

A new route for the synthesis of 4(5)‐(ω‐aminoalkyl)‐1 H‐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)‐1 H‐imidazoles 1, as precursors for a large range of histaminergic compounds, in good overall yields.