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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

2005; Royal Society of Chemistry; Volume: 3; Issue: 21 Linguagem: Inglês

10.1039/b510535h

1477-0539

Belén Abarca, Ibón Alkorta, Rafaél Ballesteros, Fernando Blanco, Mimoun Chadlaoui, José Elguero, Fatemeh Mojarrad,

Click Chemistry and Applications

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.