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Chemistry. 2014 May 12;20(20):5905-9. doi: 10.1002/chem.201402576. Epub 2014 Apr 2.

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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  • 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.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

allenoates; hydrogen shift; isocyanides; multicomponent reactions; spirocyclic oxindoles

PMID:
24700458
[PubMed - indexed for MEDLINE]
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