3 years ago

New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C−H Amination

New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C−H Amination
Jun-ichi Yoshida, Sebastian Herold, Siegfried R. Waldvogel, Lars Julian Wesenberg, Akihiro Shimizu
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. An electrified amination provides direct and highly selective access to 1,4-benzoxazin-3-ones starting from simple and readily available phenoxy acetates. This approach allows the generation of complex fused heterocycles by electro-organic synthesis.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701979

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