Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropionic acid). The formation of the key intermediate is catalyst‐controlled, and subsequent cyclization and oxidation affords pyridines in excellent yields. The method has been used for the efficient synthesis of polyarylpyridines.
Synthesis of unsymmetrically substituted pyrazines has been a challenge. The reactivity of α-imino carbenoids derived from α-diazo oxime ethers has been exploited for pyrazine synthesis, in which the reaction of α-diazo oxime ethers with 2H-azirines provides highly substituted pyrazines in good to excellent yields.
Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
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