Issue 31, 2020
From the journal:

RSC Advances

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

Nicolai A. Aksenov, ORCID logo *a   Dmitrii A. Aksenov, ORCID logo a   Nikolai A. Arutiunov,a   Daria S. Aksenova,a   Alexander V. Aksenov ORCID logo a  and  Michael Rubin ORCID logo *ab  

* Corresponding authors

a Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation

b Department of Chemistry, University of Kansas, 1567 Irving Hill Rd., Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu
Tel: +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.

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

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Article information

DOI
https://doi.org/10.1039/D0RA03520C
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

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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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