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Communication | Special issue | Vol 7, No. 2, 1977, pp.953-959
Published online, 1st January, 1970
DOI: 10.3987/S-1977-02-0953
Diazapolycyclic Compounds. XV. Opening of the Epoxide Rings in Diazaquinone Adducts: A New Condensed 1,4-Oxazepine Derivative

Berta López, Manuel Lora-Tamayo,* and Pilar Navarro

*President of the Centro Nacional de Química Orgánica, C. S. I. C., Juan de la Cierva 3 , E-28006 Madrid, Spain

Abstract

Epoxidation by m-chloroperbenzoic acid of adducts of 5-hydroxy and 5-chlorophthalazin-1.4-dione and 1,2-dimethylencyclohexane, respectively, is reported. Compounds IIa and IIb, 4a,14a-epoxide derivatives, were transformed into the 1,2-diols IIIa and IIIb by treatment with a mixture of aqueous sulfuric acid and acetone in high yields. Reaction of IIa in an alkaline solution resulted in opening of the ring C of pyridazinedione, yielding an intermediate sodium carboxylate IV which, in acidic medium, led to the formation of V, this compound being isolated in another different crystalline form VI. All structures have been determined by analytical and ir, pmr and mass spectroscopic evidences. The structure of V and VI was unambigously established by X-ray analysis.