Studies on 3-AminoindazoIes. I. Synthesis of 1- or 3-(Substituted 3-Amino)indazoles(Organic,Chemical)

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Various 1- or 3-(substituted 3-amino)indazoles with anti-inflammatory effects were synthesized by means of three methods, as follows. 1) Reactions of 3-ammoindazole (1) with acrylaniides (2a and 2b) gave amide derivatives (3a and 3b) having a carbamoylethylamino group at the 3-position of 3a and 3b. The amide derivatives (3a and 3b) were converted to thioamide derivatives (4a and 4b) by treatment with P_2S_5. Electrode reduction of 4a and 4b gave 3-(substituted 3-amino)indazoles (5a and 5b). 2) The reaction of 1 with aminoalkyl.halides (6c-r) gave 3-(substituted 3-amino)indazoles (5c-r) and 1-(substituted 3-amino)indazoles (7c-r) in a ratio of 3:1. 3) The reaction of 1 with phthalic anhydride (8) gave 3-phthaiimidoindazole (9). Compound 9 was allowed to react with aminoalkyl halides (60-r) to give 1-substituted derivatives (10s-z) of 9. Reactions of 10a-z with hydrazine hydrate gave 1-(substituted 3-amino)indazole derivatives (5s-z).
公益社団法人日本薬学会の論文
1987-06-25