Issue 10, 2016
From the journal:

Organic & Biomolecular Chemistry

Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: an unprecedented dearomatizing process†

Manuel Andreini,a   Fabien Chapellas,a   Sonia Diab,a   Karine Pasturaud,a   Serge R. Piettre,a   Julien Legrosa  and  Isabelle Chataigner ORCID logo *a  

* Corresponding authors

a Normandie Univ, COBRA, UMR 6014 et FR 3038, Univ Rouen, CNRS, INSA Rouen, IRCOF, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France
E-mail: isabelle.chataigner@univ-rouen.fr

Abstract

Nucleophilic enamines add spontaneously on heteroarenes 3-nitroindole and benzofuran to form a new C–C bond. With nitroindole 1 and enamine 2a, an unprecedented dearomatizing formal ene reaction occurs in a totally regio- and diastereo-selective manner. With 3-nitrobenzofuran 10 and enamine 2d, the reaction course is different and leads to the generation of a dienylphenol.

Graphical abstract: Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: an unprecedented dearomatizing process

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Article information

DOI
https://doi.org/10.1039/C5OB02595H
Article type
Paper
Submitted
17 Dec 2015
Accepted
08 Jan 2016
First published
12 Jan 2016

Org. Biomol. Chem., 2016,14, 2833-2839

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Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: an unprecedented dearomatizing process

M. Andreini, F. Chapellas, S. Diab, K. Pasturaud, S. R. Piettre, J. Legros and I. Chataigner, Org. Biomol. Chem., 2016, 14, 2833 DOI: 10.1039/C5OB02595H

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