Issue 31, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
20 Apr 2020
Accepted
08 May 2020
First published
14 May 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 18440-18450

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

N. A. Aksenov, D. A. Aksenov, N. A. Arutiunov, D. S. Aksenova, A. V. Aksenov and M. Rubin, RSC Adv., 2020, 10, 18440 DOI: 10.1039/D0RA03520C

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