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Synthesis reports the creation of azo-substituted benzoxazin-4-ones through base-mediated methods, suggesting new pathways for organic synthesis.
High Resolution Image Download MS PowerPoint Slide A two-step synthesis of 4 H -benzo[ d ][1,3]oxazin-4-ones bearing an azo unit at C2 from isatoic anhydrides and silylated diazenes is reported. The key step is the diazenylation of an isocyanate formed in situ by base-mediated ring opening of the isatoic anhydride. The addition of the elusive diazenyl anion proceeds without the loss of dinitrogen in the basic reaction medium. The benzoxazinone motif is subsequently established by cyclization with the Mukaiyama reagent.
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Obermayer et al. (2026) studied this question.
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