Condensation of 3-hydrazino-5,6-diphenyl-1,2,4-triazine (1) with aldop
entoses 2a-d or aldohexoses 2e-g gave the corresponding aldehydo sugar
(5,6-diphenyl-1,2,4-triazin-3-yl)hydrazones 3a-g. A one-step oxidativ
e cyclization with subsequent acetylation of these hydrazones by treat
ment with bromine in acetic acid in the presence of anhydrous sodium a
cetate followed by acetylation with acetic anhydride gave the correspo
nding 6,7-diphenyl-1,2,4-triazolo[4,3-b][1,2,4]triazines 5a-g. De-O-ac
etylation of the latter compounds with methanolic ammonia gave ol-1-yl
)-6,7-diphenyl-1,2,4-triazolo[4,3-b][1,2,4] triazines 6a-g.