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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Gold-catalyzed oxime-oxime rearrangement
Sinem Guven1, Merve Sinem Ozer1, Serdal Kaya1,2
1†Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.
Abstract:
The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the literature and is named an oxime-oxime rearrangement.
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