Issue 5, 2010
From the journal:

Organic & Biomolecular Chemistry

Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil†

Cédric Bouteiller,a   Javier Becerril-Ortega,b   Patrice Marchand,a   Olivier Nicole,b   Louisa Barré,a   Alain Buissonb  and  Cécile Perrio*a  

* Corresponding authors

a Laboratoire de Développements Méthodologiques en TEP, CEA/DSV/I2BM/CI-NAPS, UMR 6232, CNRS, Université de Caen - Basse Normandie, Cyceron, Bd Henri Becquerel, 14074 Caen Cedex, France
E-mail: perrio@cyceron.fr
Fax: +33 (0)231470275
Tel: +33 (0)231470281

b Equipe Physiopathologie de la Synapse, CEA/DSV/I2BM/CI-NAPS, UMR 6232, CNRS, Université de Caen - Basse Normandie, Cyceron, Bd Henri Becquerel, 14074 Caen Cedex, France

Abstract

An operationally simple and concise synthesis of anilinoethanolamines, as NMDA NR2B receptor antagonist ifenprodil analogues, was developed via a copper-catalyzed amination of the corresponding bromoarene. Coupling was achieved with linear primary alkylamines, α,ω-diamines, hexanolamine and benzophenone imine, as well as with aqueous ammonia, in good yields using CuI and N,N-diethylsalicylamide, 2,4-pentadione or 2-acetylcyclohexanone as catalytic systems. Amination with ethylene diamine was efficient even in the absence of an additive ligand, whereas no reaction occurred with ethanolamine whatever the conditions used. The anilinoethanolamines were evaluated as NR2B receptor antagonists in a functional inhibition assay. Aminoethylanilines displayed inhibition effects close to that of ifenprodil.

Graphical abstract: Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B923255A
Article type
Paper
Submitted
05 Nov 2009
Accepted
26 Nov 2009
First published
06 Jan 2010

Org. Biomol. Chem., 2010,8, 1111-1120

Permissions

Request permissions

Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil

C. Bouteiller, J. Becerril-Ortega, P. Marchand, O. Nicole, L. Barré, A. Buisson and C. Perrio, Org. Biomol. Chem., 2010, 8, 1111 DOI: 10.1039/B923255A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements