Isocyanide‐Based Multicomponent Reactions: Concise Synthesis of Spirocyclic Oxindoles with Molecular Complexity by Using a [1,5]‐Hydrogen Shift as the Key Step |
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Authors: | Shikuan Su Chunju Li Prof?Dr Xueshun Jia Prof?Dr Jian Li |
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Institution: | 1. Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, Shanghai, 200444 (P. R. China), Fax: (+86)?21‐66132408;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai, 200032 (P. R China) |
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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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Keywords: | allenoates hydrogen shift isocyanides multicomponent reactions spirocyclic oxindoles |
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