A simple and efficient intramolecular 1,3-dipolar azidoalkyne cycloaddition: Synthesis of 6-perfluoroalkylated fused exo-bicyclic 1,2,3-triazolo-1,4-oxazines

•The regioselective nucleophilic ring oxirane opening of perfluoroalkyl ethers and thioether terminal oxiranes 1 is realized by azide ion action.•The O-propargylation of azido-alcohols 2 produce the di(azido-alkyne) 3, which transforms immediately into the corresponding compounds 4.•Although spaced from the alkyne and azide groups, the perfluoroalkyl chain have an increasing effect on the kinetic rate of the cycloaddition.

The synthesis of new 6-perfluoroalkylated 1,2,3-triazolo-1,4-oxazine ethers and thioethers as fused exo-heterobicyclic compounds was achieved from terminal perfluoroalkyl oxiranes by azide ion ring opening and propargylation reactions followed by a quick and spontaneous 1,3-dipolar intramolecular cycloaddition reaction.

Graphical abstractThe synthesis of new 6-perfluoroalkylated 1,2,3-triazolo-1,4-oxazine ethers and thioethers, fused exo-heterobicyclic compounds was achieved from terminal perfluoroalkyl oxiranes by azide ion ring opening reaction, propargylation, followed by a quick and a spontaneous 1,3-dipolar intramolecular cycloaddition reaction is described.Figure optionsDownload full-size imageDownload as PowerPoint slide