Issue 11, 2011
From the journal:

Organic & Biomolecular Chemistry

A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes†

Sarah Zeghada,a   Ghenia Bentabed-Ababsa,*ab   Aïcha Derdour,a   Safer Abdelmounim,a   Luis R. Domingo,*c   José A. Sáez,c   Thierry Roisnel,d   Ekhlass Nassare  and  Florence Mongin*b  

* Corresponding authors

a Laboratoire de Synthèse Organique Appliquée, Faculté des Sciences de l′Université, BP 1524 Es-Senia, Oran, Algeria
E-mail: badri_sofi@yahoo.fr
Fax: +213-04158-2540
Tel: +213-79175-8768

b Chimie et Photonique Moléculaires, UMR 6510 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, Rennes Cedex, France
E-mail: florence.mongin@univ-rennes1.fr
Fax: +33-2-2323-6955
Tel: +33-2-2323-6931

c Departamento de Química Orgánica, Universidad de Valencia, Dr Moliner 50, Burjassot, Valencia, Spain
E-mail: domingo@utopia.uv.es
Fax: +34-9-6354-4328
Tel: +34-9-6354-3106

d Centre de Diffractométrie X, Sciences Chimiques de Rennes, UMR 6226 CNRS, Université de Rennes 1, Bâtiment 10B, Campus Scientifique de Beaulieu, Rennes Cedex, France

e Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Asma Fahmy Street, Heleopolis (El-Margany), Cairo, Egypt

Abstract

Reactions were performed from aryl azides on the one hand, and activated alkenes coming from β-dicarbonyl compounds or malonodinitrile on the other hand, either with recourse to conventional heating or to microwave activation, to afford 1-aryl-1H-1,2,3-triazoles. The mechanism and the regioselectivity of the reactions involving β-dicarbonyl compounds have been theoretically studied using DFT methods at the B3LYP/6-31G* level: they are domino processes comprising a tautomeric equilibrium of the β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower activation energy). The effect of non-conventional activation methods on the degradation of 1,2,3-triazolines was next studied experimentally. Finally, some of the 1,2,3-triazoles such synthesized were evaluated for their bactericidal and cytotoxic activities.

Graphical abstract: A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB05176H
Article type
Paper
Submitted
31 Jan 2011
Accepted
09 Mar 2011
First published
09 Mar 2011

Org. Biomol. Chem., 2011,9, 4295-4305

Permissions

Request permissions

A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes

S. Zeghada, G. Bentabed-Ababsa, A. Derdour, S. Abdelmounim, L. R. Domingo, J. A. Sáez, T. Roisnel, E. Nassar and F. Mongin, Org. Biomol. Chem., 2011, 9, 4295 DOI: 10.1039/C1OB05176H

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