Synthesis of Hexahydroindazole, Tetrahydro-[pyrimidoquinazolinone, benzodiisoxazolone] Derivatives and Anils from Diethyl 1,4-Cyclohexanedione-2,5-dicarboxylate
Abstract Treatment of diethyl 1,4-cyclohexanedione-2,5-dicarboxylate (1) with hydrazine hydrate in glacial acetic acid afforded the diazobicycloocatdienedicarboxylate (2) and the azine (3). On the other hand, condensation of 1 with benzenesulphonylhydrazide in ethanolic solution gave the indazole derivative (4). Interaction of 1 with urea or hydroxyl-amine afforded the tetrahydropyrimidoquinazolinone (5) and the tetrahydrobenzodi-isoxazolone (6), respectively. Treatment of 1 with aniline gave the mono-anil (7) which, when subjected to Japp-Klingemann reaction with p-anisidine gave the dihydrazonoanil (8) and their condensation with benzidine in acetic acid gave the hydrazonoketoester (9). On the other hand condensation of 7 with hydrazine hydrate in ethanolic solution afforded the azobis (5-anilinoterephthalate) (10) and the hexahydrobenzodipyrazolone (11).