Journal
CHEMICAL COMMUNICATIONS
Volume 56, Issue 24, Pages 3488-3491Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc00923g
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Funding
- Changjiang Scholars and Innovative Research Team in University [IRT17R94]
- National Natural Science Foundation of China [21662042, 81760621]
- Natural Science Foundation of Yunnan Province [2019FY003003, 2017FA003]
- Scientific and Technological Innovation Team of Green Synthesis and Activity Research of Natural-like Heterocyclic Compound Libraries in Universities of Yunnan Province
- Project of Yunnan Education Department [2018JS004]
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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 2 via 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.
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