Synthetic Studies on Fused Nitrogen-heterocycles from N-Amino-N,N '-dihydrodiazinediones (II). Condensation of N-Amino-N,N '-dihydrodiazinediones with ${\alpha},{\beta}$-Unsaturated Carbonyl Compounds

Synthetic Studies on Fused Nitrogen-heterocycles from N-Amino-N,N '-dihydrodiazinediones (II). Condensation of N-Amino-N,N '-dihydrodiazinediones with ${\alpha},{\beta}$-Unsaturated Carbonyl Compounds

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with mesityl oxide or 3-penten-2-one in acetic acid-ethanol (1:1) gave 3,4,6,9-tetrahydro-6,9-dioxopyridazino[1,2-a][1,2, 3]triazines (9,11) and 3,4,6,11-tetrahydro-6,11-dioxo[1,2,3]triazino[1,2- b]phthalazines (10,12), respectively. The condensation of 1 and 2 with crotonaldehyde, cinnamaldehyde or acrylaldehyde under the same reaction condition gave only N-alkylidene derivatlives (3-8). When the N-alkylidene derivatives isolated from the reaction of 1 and 2 with crotonaldehyde and cinnamaldehyde (3-6) were refluxed in acetic acid, the corresponding heterocyclic compounds (13-16) were obtained.