New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C-H Amination.
Lars Julian WesenbergSebastian HeroldAkihiro ShimizuJun-Ichi YoshidaSiegfried R WaldvogelPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)
1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually, the synthesis of benzoxazinones requires transition-metal catalysts and pre-functionalized substrates such as aryl halides. However, the anodic C-H amination of phenoxy acetates offers a very efficient and sustainable access to these heterocycles. The presented electrochemical protocol can be applied to a broad scope of alkylated substrates. Even tert-butyl moieties or halogen substituents are compatible with this versatile method.