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- W1926367889 abstract "Annelation reactions of six-membered rings to 1-hydrazinophthalazine, 1, were investigated. With aroyl-(acyl)pyruvates, 2, the desired system was obtained. It was found that the course of the reaction depends on the reaction condition as well as the substituted pyruvates. Thus, 3-(2-oxo-2-substituted ethyl)-4H-as-triazino-[3,4-a]phthalazin-4-one, 4, was the product when 1 reacted with 2 in alcoholic medium. The side chain tauto-merism of 4 was studied by using ir, 1H-nmr, and ms spectral methods. When 1 hydrochloride instead of 1 was reacted with 2, 3-ethoxycarbonyl-s-triazolo[3,4-a]phthalazine, 6, was the major product. The reaction of 1 with benzoylacetone in ethanol afforded the hydrazalone, 9. By ir, 1H-nmr, and 13C-nmr methods it was shown that in solution it is inolved in an enhydrazine-hydrazone as well as a ring-chain tautomerism. Compound 9 upon the action of PPA underwent dehydrative cyclization to 3-methyl-s-triazolo[3,4-a]phthalazine, 10, and 3-methyl-5-phenyl-1-(l-phthalazinyl)pyrazole, 7. The reaction of 1 with ethyl phenylpropiolate in ethanol was reported by others to give 1-(1-phthalazinyl)-3-phenyl-5-pyrazolone, 8. Upon reinvestigation of this reaction it is shown that the product actually is ethyl β-(1-phthalazinylhydrazono)benzenepropanoate, 11. Attempts to synthesize 8 were unsuccessful by this method. In the reaction of 1 with ethyl benzoylacetate the expected hydralazone 11 was easily formed which upon reaction with PPA yielded the desired species 8." @default.
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- W1926367889 date "1983-09-01" @default.
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- W1926367889 title "Ring closure reactions involving 1-hydrazinophthalazine. Reactions with 1,2,4-tricarbonyl and 1,3-dicarbonyl compounds" @default.
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- W1926367889 doi "https://doi.org/10.1002/jhet.5570200517" @default.
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