期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 20, 页码 5905-5909出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402576
关键词
allenoates; hydrogen shift; isocyanides; multicomponent reactions; spirocyclic oxindoles
资金
- National Natural Science Foundation of China [21272148, 21272147]
- Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science
A concise multicomponent reaction of isocyanide, -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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