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

Nicolai A. Aksenov, Dmitrii A. Aksenov, Nikolai A. Arutiunov, Daria S. Aksenova, Alexander V. Aksenov, Michael Rubin
2020 RSC Advances  
An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from -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.
doi:10.1039/d0ra03520c fatcat:5kralfpcezecpmnmfpq4vwmoki