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Issue 24, 2020
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Cascade reaction of isatins with nitro-substituted enamines: highly selective synthesis of functionalized (Z)-3-(1-(arylamino)-2-oxoarylidene)indolin-2-ones

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Abstract

A novel protocol for the construction of functionalized (Z)-3-(1(-arylamino)-2-oxoarylidene)indolin-2-ones (AOIDOs) from isatins 1 with nitro-substituted enamines 2via an unprecedented cascade reaction catalyzed by sulfamic acid is developed. The AOIDOs are prepared by simply refluxing a mixture of isatins with a wide variety of nitro-substituted enamines. Interestingly, the AOIDOs 3 were formed through the novel cascade reaction involving a unique cleavage of two C–N bonds of the nitro-substituted enamines. Overall, the novel reaction is accomplished by the formation of three new bonds and the cleavage of two C–N bonds in a single step. This protocol can be used in the synthesis of a wide variety of AOIDOs and is suitable for combinatorial and parallel syntheses of natural-like AOIDO products.

Graphical abstract: Cascade reaction of isatins with nitro-substituted enamines: highly selective synthesis of functionalized (Z)-3-(1-(arylamino)-2-oxoarylidene)indolin-2-ones

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Supplementary files

Article information


Submitted
06 Feb 2020
Accepted
02 Mar 2020
First published
03 Mar 2020

Chem. Commun., 2020,56, 3488-3491
Article type
Communication

Cascade reaction of isatins with nitro-substituted enamines: highly selective synthesis of functionalized (Z)-3-(1-(arylamino)-2-oxoarylidene)indolin-2-ones

C. Zhang, R. Huang, X. Qing, J. Lin and S. Yan, Chem. Commun., 2020, 56, 3488
DOI: 10.1039/D0CC00923G

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