PyrazoloneおよびPyrazole誘導体の合成研究(第1報)3位に官能基を有するPyrazolone誘導体の合成

概要

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Methyl 1-substituted 5-oxo-3-pyrazolin-3-yl acetates (IV) were synthesized by the reaction of methyl 3-oxoglutarate (I) with 1-substituted hydrazine (III). An attempt was made to introduce a methyl group into 2-position of methyl 1-phenyl-5-oxo-3-pyrazolin-3-yl acetate (IVa) but it was found that a pyrazole-type compound (XI) was also produced besides the pyrazolone type (VIIIa) through this process. On the basis of this result, 1,2-disubstituted 5-oxo-3-pyrazolin-3-yl acetic acids (VIII) were synthesized by introduction of the corresponding substituent into 2-position of IV. 1-Substituted 5-oxo-3-pyrazolin-3-yl acetic acid (V) and VIII were easily pyrolyzed and changed into 3-methylpyrazolone type compounds (the former into VI and the latter into IX). The activity of VIII as an antipyretic, analgesic, and antispasmodic was tested but they proved to be no better than the well-known medicines.
公益社団法人日本薬学会の論文
1972-09-25