Issue 25, 2012
From the journal:

Organic & Biomolecular Chemistry

Study of N1-alkylation of indoles from the reaction of 2(or 3)-aminoindole-3-(or 2)carbonitriles with DMF-dialkylacetals†

Yvonnick Loidreau,ab   Sigismund Melissen,b   Vincent Levacher,bc   Cédric Logé,d   Jérôme Graton,e   Jean-Yves Le Questel*e  and  Thierry Besson*ab  

* Corresponding authors

a Université de Rouen, U.F.R. Médecine – Pharmacie, 22 boulevard Gambetta, 76183 Rouen Cedex 1, France
E-mail: thierry.besson@univ-rouen.fr
Fax: +33(0)235592965
Tel: +33(0)235592904

b CNRS, Laboratoire C.O.B.R.A., UMR 6014 & FR3038, Institut de Recherche en Chimie Organique Fine (I.R.C.O.F.) rue Tesnière, 76130 Mont Saint-Aignan, France

c INSA de Rouen, Avenue de l'Université, 76801 Saint-Étienne-du-Rouvray Cedex, France

d Université de Nantes, Nantes Atlantique Universités, laboratorie de Chimie thérapeutique, Cibles et Médicaments des Infections, de l'Immunité et du cancer, IICiMed UPRES EA 1155, U.F.R. Sciences Pharmaceutiques et Biologiques, 1 rue Gaston Veil, 44035 Nantes, France

e Université de Nantes, Chimie et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR CNRS 6230, 2 rue de la Houssinière – BP 92208, 44322 Nantes Cedex 3, France
E-mail: jean-yves.le-questel@univ-nantes.fr
Fax: +33(0)251125712
Tel: +33(0)251125563

Abstract

The condensation of 2-aminoindole-3-carbonitriles and their 3-aminoindole-2-carbonitrile isomers with various DMF-dialkoxyacetals was investigated under microwaves. The appearance of reactive and versatile alkoxyiminium species allowed convenient access to indole precursors of building blocks with potential biological activity. The experimental results have been rationalised using DFT calculations of theoretical descriptors based on the electrostatic potential.

Graphical abstract: Study of N1-alkylation of indoles from the reaction of 2(or 3)-aminoindole-3-(or 2)carbonitriles with DMF-dialkylacetals

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Article information

DOI
https://doi.org/10.1039/C2OB25747E
Article type
Paper
Submitted
27 Jan 2012
Accepted
04 May 2012
First published
04 May 2012

Org. Biomol. Chem., 2012,10, 4916-4925

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Study of N1-alkylation of indoles from the reaction of 2(or 3)-aminoindole-3-(or 2)carbonitriles with DMF-dialkylacetals

Y. Loidreau, S. Melissen, V. Levacher, C. Logé, J. Graton, J. Le Questel and T. Besson, Org. Biomol. Chem., 2012, 10, 4916 DOI: 10.1039/C2OB25747E

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