New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C-H Amination
Lars Julian Wesenberg1, Sebastian Herold1,2, Akihiro Shimizu3
1Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Abstract:
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.
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