Studies of Rearrangement Reaction. VIII. Ring-Contraction from Pyridazinone Derivatives to Pyrazolone Derivatives. (3).
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The behaviors of various 4,5-di-and 3,4,5-trisubstituted 1-phenyl-6 (1H)-pyridazinone against caustic alkali and hydrobromic acid were investigated. From these data, the mechanism of the ring-contraction from pyridazinone to pyrazolone, as shown in Chart 1,was discussed. Action of 1-phenyl-4,5-dichloro-6 (1H)-pyridazinone with boiling caustic alkali took place the ring-contraction to give unexpected 1-phenyl-3-hydroxy-5-pyrazole-carboxylic acid. The mechanism of this reaction was also assumed as shown in Chart 4. Moreover, the reactivity of chlorines on 1-phenyl-3,4,5-trichloro-6 (1H)-pyridazinone was elucidated to increase in the order 4-, 5-, 3-position from the result of its methoxylation reaction.
- 社団法人日本薬学会の論文
- 1964-02-25
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