Issue 21, 2005
From the journal:

Organic & Biomolecular Chemistry

3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines. An experimental and theoretical (DFT) study of the ring–chain isomerization

Belén Abarca,*a   Ibon Alkorta,b   Rafael Ballesteros,a   Fernando Blanco,a   Mimoun Chadlaoui,a   José Elguero*b  and  Fatemeh Mojarrada  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Avda. Vicente Andrés Estellés s/n, Burjassot (Valencia), Spain
E-mail: Belen.Abarca@uv.es
Fax: 34 9635 44939
Tel: 34 9635 44933

b Instituto de Química Médica, CSIC, Juan de la Cierva 3, Madrid, Spain
E-mail: iqmbe17@iqm.csic.es
Fax: 34 9156 44853
Tel: 34 9156 22900

Abstract

An experimental (1H NMR) and theoretical (DFT) study of the ring–chain–ring isomerization of 3-(2-pyridyl)-[1,2,3]triazolo[1,5-a]pyrid-7-yl derivatives (A) into 6-{[1,2,3]triazolo[1,5-a]pyrid-3-yl}-2-pyridyl derivatives (B) has been carried out. Based on the calculations, a mechanism of several steps will be proposed. The experimental results as well as the calculations lead to the conclusion that the A–B ratio depends on the electronic properties of the substituents.

Graphical abstract: 3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines. An experimental and theoretical (DFT) study of the ring–chain isomerization

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Article information

DOI
https://doi.org/10.1039/B510535H
Article type
Paper
Submitted
22 Jul 2005
Accepted
24 Aug 2005
First published
23 Sep 2005

Org. Biomol. Chem., 2005,3, 3905-3910

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3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines. An experimental and theoretical (DFT) study of the ring–chain isomerization

B. Abarca, I. Alkorta, R. Ballesteros, F. Blanco, M. Chadlaoui, J. Elguero and F. Mojarrad, Org. Biomol. Chem., 2005, 3, 3905 DOI: 10.1039/B510535H

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