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

doi:10.1039/d0ra03520c

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

RSC Adv. 2020 May 14;10(31):18440-18450. doi: 10.1039/d0ra03520c. eCollection 2020 May 10.

Authors

Nicolai A Aksenov¹, Dmitrii A Aksenov¹, Nikolai A Arutiunov¹, Daria S Aksenova¹, Alexander V Aksenov¹, Michael Rubin^{1

2}

Affiliations

¹ Department of Chemistry, North Caucasus Federal University 1a Pushkin St. Stavropol 355009 Russian Federation.
² Department of Chemistry, University of Kansas 1567 Irving Hill Rd. Lawrence KS 66045-7582 USA mrubin@ku.edu +1-785-864-5071.

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.