Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides

✍ Scribed by Ryan M. Stolley; Michael T. Maczka; Janis Louie

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 463 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100428

✦ Synopsis

Abstract

A variety of bicyclic N,N‐disubstituted 2‐aminopyridines have been prepared from diynes and cyanamides by nickel‐catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2‐aminopyridines in good to excellent yields. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides with diverse functional group tolerance were used. The intermolecular version employing 3‐hexyne and N‐cyanopyrrolidine also afforded the desired N,N‐disubstituted 2‐aminopyridine in good yield.