Studies on Condensed Triazines and Related Compounds

Acenaphthone monosemicarbazone was cyclised to acenaphtheno[1,2‐ ‐e ]1,2,4‐triazine‐3‐one ( 2 ). Its N ‐alkyl derivative 3 was prepared by the reaction with an alkyl halide in alkaline medium. The triazinone 2 was further converted into the corresponding chloro compound 4 which underwent nucleophilic substitutions with hydrazine and amines. 3‐Hydrazinoacenaphtheno[1,2‐ e ]‐1,2,4‐triazine ( 9 ) was transformed into pyrazolotriazines 12, 13, 14 by reaction with acetylacetone, ethyl acetoacetate and ethyl ethoxymethylenecyanoacetate. With formic acid and nitrous acid 9 yielded the new heterocycles acenaphtheno [1,2‐ e ]‐1,2,4‐triazino[2,3‐ d ]‐1,2,4‐triazole ( 11 ) and acenaphtheno[1,2‐ e ]‐1,2,4‐triazino[2,3‐ d ]‐tetrazole ( 10 ).