Molecular Diversity of the Three-Component Reactions of N-Benzylbenzimidazolium Salts, Aromatic Aldehydes, and Active Methylene Compounds

✍ Scribed by Li Hui; Yu-Xiu Jin; Jin-Xiu Wang; Chao-Guo Yan

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 464 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101199

✦ Synopsis

Abstract

The three‐component reactions of in‐situ‐formed N‐benzylbenzimidazolium salts, aromatic aldehydes, and active methylene compounds in the presence of triethylamine showed very interesting molecular diversity. The reactions with Meldrum's acid or barbiturate in acetonitrile gave a series of the novel zwitterionic salts in high yields. Under similar reaction conditions, the reactions with malononitrile or ethyl cyanoacetate produced functionalized pyrrolo[1,2‐a]benzimidazoles in good yields with an unprecedented regioselectivity.