Wesenberg Lars Julian, Herold Sebastian, Shimizu Akihiro, Yoshida Jun-Ichi, Waldvogel Siegfried R
Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Graduate School Material Science in Mainz, Johannes Gutenberg Universität Mainz, Staudingerweg 9, 55128, Mainz, Germany.
Chemistry. 2017 Sep 7;23(50):12096-12099. doi: 10.1002/chem.201701979. Epub 2017 Jul 10.
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.
1,4-苯并恶嗪-3-酮是天然产物和生物活性化合物中的重要结构基序。通常，苯并恶嗪酮的合成需要过渡金属催化剂和预官能化底物，如芳基卤化物。然而，苯氧基乙酸酯的阳极C-H胺化提供了一种非常有效且可持续的途径来合成这些杂环化合物。所提出的电化学方法可应用于广泛的烷基化底物。甚至叔丁基部分或卤素取代基也与这种通用方法兼容。
