Phthalazine 誘導体に関する研究(第6報) : 1-Methylおよび1-BenzylphthalazineのN-Oxidationについて

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N-oxidation of 1-methyl-(I) and 1-benzyl-phthalazine (II) was attempted at lower than 10° in the mixed solvents of chloroform and ether using monoperphthalic acid. 2-Oxide (I_2) and 3-oxide (I_3) were produced from I in a 1 : 2 ratio and from II 2-oxide (II_2) and 3-Oxide (II_3) in almost a 3 : 1 ratio. The position of N-oxide groups were determined by the following procedures. To I_2 and I_3,phenylmagnesium bromide was reacted respectively and the reaction solution was treated with p-benzoquinone to 2-oxide (III_2) and 3-oxide (III_3) of 1-methyl-4-phenylphthalazine (III). III_2 was confirmed by the synthesis separately carried out in reacting 1-phenylphthalazine 3-oxide (IV_3) with methylmagnesium iodide. Therefore, the structure of I_2 was decided and that of I_3 might be suggested. Similar procedures were made in the determination of the structures of II_2 and II_3. It was reported that only 2-oxide (III_2) was produced from 1-methyl-4-phenylphthalazine (III) and that from 1-isopropyl-4-phenylphthalazine (VII), only 3-oxide (VII_3) was produced (Chart 3). N-oxidation of 1-ethyl-4-phenylphthalazine (IX) was attempted and only 2-oxide (IX_2) was obtained (Chart 4).
公益社団法人日本薬学会の論文
1968-10-25