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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Isocyanide-based multicomponent reactions: concise synthesis of spirocyclic oxindoles with molecular complexity by
Shikuan Su1, Chunju Li, Xueshun Jia
1Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, Shanghai, 200444 (P. R. China), Fax: (+86) 21-66132408.
Abstract:
A concise multicomponent reaction of isocyanide, α-substituted allenoate, and methyleneindolinone has been disclosed. This protocol provides a fast and straightforward approach to synthesize unusual tricyclic oxindoles in an efficient and atom-economic manner. Mechanistically, the present cycloaddition may proceed through a cascade sequence involving double Michael addition, double cyclization, double [1,5]-hydrogen shift, and group migration. The introduction of a special alkyl group to the allenoate is believed to play a key role in the cascade reaction. This method also features a broad substrate scope, which is particularly useful for the delivery of a large number of compounds.
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