Pyridazines. II. Intramolecular Cycloaddition of 3-Substituted-6-[2-(2-methylallyl) phenoxy] pyridazines

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Heating of 3-phenyl-, 3-methyl, and 3-chloro-6-[2-(2-methylallyl) phenoxy] pyridazine in diethylaniline or without a solvent afforded 2-substituted-9a-methyl-1,9a-dihydroxanthenes, which are previously unknown group of compounds. The mechanism of this reaction may be explained by an intramolecular cycloaddition between pyridazine nucleus and the allylic side chain to give the (4+2)π adduct followed by N_2 elimination. Similarly, cyclization of 1-phenyl-4-[2-(1-methylallyl)-1-naphthyloxy] phthalazine gave 5-phenyl-6a-methyl-6a, 12a-dihydro-7H-benzo [c] xanthene.
公益社団法人日本薬学会の論文
1976-07-25