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■ Factors Influencing the Pathway of Reactions of 1-Hydrazinophthalazine with Di- and Tricarbonyl Compounds

Adel Amer, Klaus Weisz, and Hans Zimmer

*Frank J. Seiler Research Laboratory, U.S.A.F. Academy, CO 80840, U.S.A.

Abstract

The reaction of 1-hydrazinophthalazine (hydralazine) (1) with substituted ethyl benzoylpyruvates (3) leads under neutral reaction conditions to 3-[2-oxo-2-(substituted phenyl)ethyl]-4H-as-triazino[3,4-a]phthalazin-5-ones (4).Under acidic but otherwise identical conditions depending on the substituent of 3, 4 and/or 3-carbethoxya-triamlo[3,4-a]phthalazine (5) with simultaneous elimination of the appropriate acetophenone were obtained. 1-HCI and substituted ethyl cinnamoylpyruvates (6a-e) give rise to formation of 1-(1-phthalazinyl)-3-carbethoxy-5-(3-or 4-substituted styry1)pyrazoles (7). Under neutral conditions the reaction of 1 with 6 gives as-triazino[3,4-a]phthalazine (8). The structures of 4, 5, 7, and 8 are based on elemental analysis and extensive ms- and ¹H-nmr investigations.