縮合環を有するPyridazine誘導体に関する研究(第4報)7-Methoxy-1-phenyl-1H-pyrazolo[3,4-d]pyridazine 5-Oxideの化学的性質

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Chemical properties of 7-methoxy-1-phenyl-1H-pyrazolo [3,4-d] pyridazine 5-oxide (V) obtained in the reaction of 7-methoxy-1-phenyl-1H-pyrazolo [3,4-d] pyridazine (IV) with m-chloroperbenzoic acid were studied. Compound V reacted with nucleophiles to give 4 (R^2), 7 (R^1)-disubstituted 1-phenyl-1H-pyrazolo [3,4-d] pyridazine or the ring fission product, methyl 4 (R^8)-substituted 1-phenyl-1H-pyrazole-5-carboxylate. The reaction of V with each of phosphoryl chloride and sulfuryl chloride gave VI (R^2=Cl, R^1=OCH_3) and XI (R^2=Cl, R^1=OH). In the case of the reaction of V with tosyl chloride, XII (R^3=CH (-Cl)-p-tosyl) was obtained together with VI and XI. The reaction of V with potassium hydroxide solution gave IX (R^2=H, R^1=OH, 5-oxide). The reaction of V with ethyl cyanoacetate in acetic anhydride gave XIII (R^2=NC-CH-CO_2C_2H_5,R^1=OCH_3). The Grignard reaction of V with methylmagnesium iodide and ethylmagnesium bromide gave XIVa (R^2=CH_3,R^1=OCH_3) and XIVb (R^2=C_2H_5,R^1=OCH_3), respectively. Application of the Reissert reaction to V resulted in the formation of XVI (R^3=CH=C (-OCH_3)-(4-formyl-1-phenyl-1H-pyrazol-5-yl). The reaction of V with acetic anhydride afforded XVII (R^2=OH, R^1=OCH_3), XVIII (R^3=CH (-COCH_3)-O-COCH_3), and XIX ((R^3=CH=)_2). The reaction of V with acetyl chloride afforded XI, XXa (R^3=CH (-COCH_3)-R^4,R^4=4-chloro-6,7-dihydro-7-oxo-1-phenyl-1H-pyrazolo [3,4-d] pyridazin-6-yl) and XXI (R^3=CH_2-R^4). A similar ring fission occurred in the reaction of V with benzoly chloride to afford XXb (R^3=CH (-COPh)-R^4), XXI, and XIX. The reaction of V with dimethyl acetylenedicarboxylate afforded 7-methoxy-1-phenyl-1H-pyrazolo [3,4-d] pyridazinium 3-methoxy-1-methoxycarbonyl-2,3-dioxopropylide (XXII), trimethyl 9-methoxy-1-phenyl-1H-pyrazolo [3,4-d] pyrrolo [1,2-b] pyridazine-4,5,6-tricarboxylate (XXIII), and methyl 5-methoxycarbonyl-6-methoxy-α-oxo-1-phenyl-1,5H-cyclopenta [c]-pyrazol-5-ethanoate (XXIV). It is considered that the ring fission products are formed by the cleavage of pyridazine ring accompanied with the liberation of nitrogen.
社団法人日本薬学会の論文
1985-02-25

縮合環を有するPyridazine誘導体に関する研究(第4報)7-Methoxy-1-phenyl-1H-pyrazolo[3,4-d]pyridazine 5-Oxideの化学的性質

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