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Thermolysis of Geminal Diazides: Reagent-Free Synthesis of 3‑Hydroxypyridines

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journal contribution
posted on 16.12.2016 by Hellmuth Erhardt, Kevin A. Kunz, Stefan F. Kirsch
An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β-ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described.