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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Dearomative Migratory Rearrangement of 2-Oxypyridines Enabled by α-Imino Rhodium Carbene
Guangyang Xu1, Ying Shao1, Shengbiao Tang1
1Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
Abstract:
The unprecedented dearomative migratory rearrangement reactions of 2-oxypyridines with N-sulfonyl-1,2,3-triazoles have been developed under rhodium catalysis, providing a reliable and efficient protocol for accessing N-substituted 2-pyridones. These two distinct rearrangements feature the controllable 1,4-migration of a carbonate group from O-to-C as well as the O-to-N 1,6-migration of an acyl group via α-imino rhodium carbene transfer. Moreover, the reaction of pyridotriazoles with 2-oxypyridines delivers the 1,4-migration products in high efficiency.
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