Synthesis of new 1H-pyridazine derivatives peri-annelated with acenaphthene and acenaphthylene

The reaction of 6-acetyl-5-hydroxyacenaphthene with methylhydrazine afforded 1,3-dimethyl-1H-6,7-dihydroacenaphtho[5,6-de]pyridazine. Its dehydrogenation with chloranil gave 1,3-dimethyl-]H-acenaphtho[5,6-de]pyridazine, which is a heteroaromatic compound with an essentially new topology of the pi-system. The reaction of 3-methyl-1H-6,7-dihydroacenaphtho [5,6-de] pyridazine with 3,5-di-tert-butyl-1,2-benzoquinone yielded a dimer containing the acenaphthene and acenaphthylene moieties of peri-annelated 1H-1,2-diazines connected in positions 1' and 9.