New Syntheses of Substituted Pyridines via Bromine–Magnesium Exchange

✍ Scribed by François Trécourt; Gilles Breton; Véronique Bonnet; Florence Mongin; Francis Marsais; Guy Quéguiner

• Book ID: 104202506
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 233 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00027-2

✦ Synopsis

Bromine-magnesium exchange using iPrMgCl in THF at room temperature on 2-, 3-and 4-bromopyridines allowed the synthesis of various functionalized pyridines. The methodology was successfully used for the synthesis of 4-azaxanthone. Moreover, single exchange reactions observed on 2,6-, 3,5-, 2,3-and 2,5-dibromopyridines, with complete regioselectivity in the case of 2,3-and 2,5dibromopyridines, afforded substituted bromopyridines, which were then involved in a second exchange step to provide difunctionalized pyridines.