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Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α‑Diazo Oxime Ethers

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posted on 2017-09-04, 00:00 authored by Sangjune Park, Hyunseok Kim, Jeong-Yu Son, Kyusik Um, Sooho Lee, Yonghyeon Baek, Boram Seo, Phil Ho Lee
The Cu-catalyzed, formal aza-[3 + 2] cycloaddition reaction of pyridine derivatives with α-diazo oxime ethers in trifluoroethanol was used to synthesize imidazopyridines via the release of molecular nitrogen and elimination of alcohol. These methods enabled modular synthesis of a wide range of N-heterobicyclic compounds such as imidazo­pyridazines, imidazo­pyrimidines, and imidazo­pyrazines with an α-imino Cu-carbenoid generated from the α-diazo oxime ethers and copper.