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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 11, Number 1
BKCSDE 11(1)
January 20, 1990 

Synthetic Studies on Fused Nitrogen-heterocycles from N-Amino-N,N '-dihydrodiazinediones (Ⅱ). Condensation of N-Amino-N,N '-dihydrodiazinediones with α,β-Unsaturated Carbonyl Compounds
Sung Chul Shin, Kyung Ho Kang, Youn Young Lee*, Yang Mo Goo
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.
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