Facile access to 2,2-disubstituted indolin-3-ones via a cascade Fischer indolization/Claisen rearrangement reaction.

Chem Commun (Camb) 2017 Jul;53(54):7485-7488

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China.

An efficient approach for the synthesis of 2,2-disubstituted indolin-3-ones is described. From readily accessible aryl hydrazines and allyloxyketones, 2,2-disubstituted indolin-3-ones could be obtained in good to excellent yields under mild reaction conditions via a cascade Fischer indolization/Claisen rearrangement process. This protocol provides a facile entry to 2,2-disubstituted indolin-3-ones, which have been applied in the construction of the benzofuroindoline framework related to Phalarine.

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July 2017
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References

(Supplied by CrossRef)

Liu et al.
Org. Lett. 2007

Karadeolian et al.
Angew. Chem., Int. Ed. 2010

Lee et al.
Org. Lett. 2011

Zhang et al.
Angew. Chem., Int. Ed. 2011

Patel et al.
J. Org. Chem. 2012

Wu et al.
Org. Lett. 2012

Greshock et al.
Angew. Chem., Int. Ed. 2007

Artman et al.
J. Am. Chem. Soc. 2007

Greshock et al.
Angew. Chem., Int. Ed. 2008

Finefield et al.
Org. Lett. 2011

Mercado-Marin et al.
Chem. Sci. 2015

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