Preparation of some N-aminotriazolo-pyridines and -quinolines, their oxidation with lead tetra-acetate, and the trapping of the resulting pyridynes and quinolynes with tetraphenylcyclopentadienone (tetracyclone)

Abstract

The preparations of 1-aminotriazolo[4,5-c]pyridine (4), 3-aminotriazolo[4,5-b]pyridine (9), 1-aminotriazolo-[4,5-c]quinoline (14), and 3-aminotriazolo-[4,5-b]quinoline (18) are described. The oxidation of these compounds with lead tetra-acetate in the presence of tetraphenylcyclopentadienone gave the products expected from the trapping of 3,4-pyridyne, 2,3-pyridyne, 3,4-quinolyne, and 2,3-quinolyne respectively. The adducts of 2,3-pyridyne and 2,3-quinolyne were obtained only in low yield.