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.

The 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 as PowerPoint slide