4-Diazo-3,5-dimethylpyrazoleの反応性(第2報)4-Alkyl(or Aryl)azo-3,5-dimethylpyrazole誘導体の合成に際しての知見

概要

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Coupling reaction of 4-diazo-3,5-dimethylpyrazole (1) with compounds possessing active methylene or methyl group and phenolic compounds was examined. Of these, the reaction of 1 with phenol was mechanistically discussed, because it proceeded with ease to afford bis-azo compound (13) in the main, even when equimoles of the two reagents were used. It was also found that 6-(3,5-dimethylpyrazol-4-ylazo)-1H, 4H-3-methylpyrarazolo-[4,3-c] pyrazole (23) was formed via both intramolecular and intermolecular coupling reactions when 1 was heated in tert-butanol, contrasting with the previous finding^<1)> that the same reaction yielded 1H, 4H-3-methy1pyrazo1o [4,3-c] pyrazole (10) in the presence of acetic acid. Additionally, the reaction of alkyl- or aryl-magnesium halide with 1 was undertaken and its usefulness was found for the preparative of 4-arylazo-3,5-dimethylpyrazole which has not been obtained by the coupling reactions.
公益社団法人日本薬学会の論文
1974-01-25