Synthesis of Heterocycles by Intramolecular Nucleophilic Substitution at an Electron-Deficient sp2 Nitrogen Atom

✍ Scribed by Jarosław Sączewski; Maria Gdaniec

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 337 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200901520

✦ Synopsis

Abstract

2‐Aryl(arylsulfonyl)‐6,7‐dihydro‐2__H__‐imidazo[2,1‐c][1,2,4]triazol‐3(5__H__)‐ones and 3‐arylimino‐6,7‐dihydroimidazo[2,1‐c][1,2,4]thiadiazoles have been synthesized by intramolecular nucleophilic substitution reactions at the electron‐deficient sp^2^ nitrogen atom of 2‐(hydroxyimino)imidazolidine O‐sulfonate. The displacement of the sulfate leaving group by both nitrogen and sulfur anionic nucleophiles proceeds exothermically by in‐plane S~N~2σ nucleophilic substitution.