Pyridazine 1,2-Dioxide類の研究(第2報)3,6-Dimethylpyridazine 1,2-Dioxideの求電子反応

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Treatment of 3,6-dimethylpyridazine 1,2-dioxide (I) with nitric acid in sulfuric acid at room temperature gave 4-nitro-3,6-dimethylpyridazine 1,2-dioxide (II) as yellow needles in a good yield. Heating of I with sulfuric and nitric acids at 70° gave 4-nitro-3,6-dimethylpyridazine 1-oxide (IV), 4-nitro-3,6-dimethylpyridazine 2-oxide (V), and 3,6-dimethylpyridazine 1-oxide (III) with the formation of II. On the other hand, nitration of I with benzoyl nitrate in chloroform afforded II in a very poor yield. I was highly resistant to other electrophilic reactions, such as bromination, sulfonation, and Mannich reaction. Condensation of I and benzaldehyde, with sodium methoxide as a catalyst, resulted in the formation of 3,6-distyrylpyridazine 1,2-dioxide (VII).
公益社団法人日本薬学会の論文
1973-01-25