Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines
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- Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines
- Loy, Nicole S. Y.; Singh, Alok; Xu, Xianxiu; Park, Cheol-Min
- carbenoids; electrocyclic reactions; heterocycle; ring expansion; synthetic methods
- Issue Date
- WILEY-V C H VERLAG GMBH
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.52, no.8, pp.2212 - 2216
- 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.
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