Synthesis of New Bis-imidazole Derivatives

✍ Scribed by Marcin Jasiński; Grzegorz Mlostoń; Paulina Mucha; Anthony Linden; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 189 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790186

✦ Synopsis

Abstract

The reaction of aldimines with α‐(hydroxyimino) ketones of type 10 (1,2‐diketone monooximes) was used to prepare 2‐unsubstituted imidazole 3‐oxides 11 bearing an alkanol chain at N(1) (Scheme 2, Table 1). These products were transformed into the corresponding 2__H__‐imidazol‐2‐ones 13 and 2__H__‐imidazole‐2‐thiones 14 by treatment with Ac~2~O and 2,2,4,4‐tetramethylcyclobutane‐1,3‐dithione, respectively (Scheme 3). The three‐component reaction of 10, formaldehyde, and an alkane‐1,ω‐diamine 15 gave the bis[1__H__‐imidazole 3‐oxides] 16 (Scheme 4, Table 2). With Ac~2~O, 2,2,4,4‐tetramethylcyclobutane‐1,3‐dithione or Raney‐Ni, the latter reacted to give the corresponding bis[2__H__‐imidazol‐2‐ones] 19 and 20, bis[2__H__‐imidazol‐2‐thione] 21, and bis[imidazole] 22, respectively (Schemes 5 and 6). The structures of 11a and 16b were established by X‐ray crystallography.