Oligoethylene glycol diglycidyl ethers 1 were converted by the action of sodium azide in the hydro-methanolic medium into the corresponding (azido alcohols) 2. The latter react with 2-chloroacetonitrile in the presence of potassium t-butoxide in one pot, leading to new condensed ring systems 1,5-tetrazole 4 via an intramolecular [2+3] cycloaddition reaction. The present method avoids the formation and isolation of azido nitrile 3 generated in situ and also the use of any catalyst.
L. Aroua, A. Baklouti
oligoethylene glycol diglycidyl ether, tetrazole, sodium azide, chloroacetonitrile, potassium t-butoxide, intramolecular [2+3] cycloaddition reaction