縮合環を有するPyridazine誘導体に関する研究(第3報)4,7-Dichloro-1-phenyl-1H-pyrazolo[3,4-d]pyridazineとCarbanion類との反応

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4,7-Dichioro-1-phenyl-1H-pyrazolo [3,4-d] pyridazine (I) reacted with active methylene compounds i.e. ethyl cyanoacetate (IIa), ethyl acetoacetate (IIb), diethyl malonate (IIc), malononitrile (IId) and phenylacetonitrile (IIe) in the presence of sodium hydride in refluxing benzene to afford the corresponding 4-substituted (R^1) 7-chloro-1-phenyl-1H-pyrazolo [3,4-d] pyridazine (III) or 7-substituted (R^2) 4-chloro-1-phenyl-1H-pyrazolo [3,4-d]-pyridazine (IV) i.e. IIIa (R^1=NC-CH-CO_2C_2H_5), IVa (R^2=NC-CH-CO_2C_2H_5), IVb (R^2=CH_8CO-CH-CO_2C_2H_5), IVc (R^2=CH (CO_2C_2H_5)_2), IIId (R^1=CH (CN)_2), IIIe (R^1=NC-CH-Ph). Compound I also reacted with ketones having an active methylene group i.e. acetophenone (IIf), propiophenone (IIg), acetone (IIh) and diethyl ketone (IIi) in the presence of sodium hydride in refluxing toluene to afford the corresponding 4-substituted (R^1) 7-chloro-1-phenyl-1H-pyrazolo [3,4-d] pyridazine (IX), 7-substituted (R^2) 4-chloro-1-phenyl-1H-pyrazolo [3,4-d] pyridazine (X) or 4,7-disubstituted (R^3) 1-phenyl-1H-pyrazolo [3,4-d] pyridazine (XI) i.e. IXa (R^1=CH_2COPh), Xa (R^2=CH_2COPh), XIa (R^3=CH_2COPh), XIb (R^3=CH_3-CH-COPh), IXc (R^1=CH_2COCH_3), Xc (R^2=CH_2COCH_3), XIc (R^3=CH_2COCH_3), IXd (R^1=CH_3-CH-COC_2H_5).
社団法人日本薬学会の論文
1985-02-25