REGIOISOMERIC FORMATION OF ACENAPHTHO[1,2-E][1,2,4]TRIAZOLO[3,4-C] [1,2,4]TRIAZINES AND THEIR ACYCLIC C-NUCLEOSIDE ANALOGS

The oxidative cyclization of the ethylidene derivative of 3-hydrazinoa cenaphtho[1,2-e][1,2,4]triazine (2) gave regioselectively the angular isomer aphtho[1,2-e][1,2,4]triazolo[3,4-c][1,2,4]triazine (5). Its lin ear isomer aphtho[1,2-e][1,2,4]triazolo[4,3-b][1,2,4]triazine (4) was synthesized by the condensation of acenaphthenequinone (6) with 3,4-di amino-5-methyl-4H-1,2,4-triazole. Condensation of 2 with a number of m onosaccharides afforded the respective hydrazones 9 whose oxidative cy clization gave the corresponding (polyhydroxyalkyl)acenaphtho[1,2-e][1 ,2,4]triazine (10). Acetylation of 9 and 10 gave lidene)hydriazino]ace naphtho[1,2-e][1,2,4]triazine (11) and aphtho[1,2-e][1,2,4]triazolo[3, 4-c][1,2,4]triazine (13) respectively. Periodate oxidation of 9e gave hylidenehydrazino)acenaphtho[1,2-e][1,2,4]triazine (14).