Eur. J. Org. Chem. 5765-5778 (2009)

DOI: 10.1002/ejoc.200900818

3-(Pyridin-2-yl)[1,2,3]triazolo[1,5-a]quinoline: A Theoretical and Experimental Analysis of Ring-Chain Isomerisation

In the course of the synthesis of new fluorophores for molecular recognition an experimental (1H NMR) and theoretical (DFT) study of the ring-chain isomerism of 3-(pyridin-2-yl)[1,2,3]triazolo[1,5-a]quinoline derivatives (A) into 2-([1,2,3]triazolo[1,5-a]pyridin-3-yl)quinoline derivatives (B) has been carried out. The rearrangement is influenced by steric and electronic effects of the substituents present on the quinoline ring.