Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones?

RSC Advances Pub Date: 2020-05-14 DOI: 10.1039/D0RA03520C

Abstract

An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from ortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically related to the Baeyer–Drewson reaction.

Graphical abstract: Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
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