Condensed Pyridazines. V. Reactions of 7-(Methylsulfonyl)-1-phenyl-1H-1,2,3-triazolo[4,5-d]pyridazine with Methoxide Ion, Grignard Reagents, Hydrazines, and Amines(Organic,Chemical)

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概要

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• Nucleophiles were found to react with 7-(methylsulfonyl)-1-phenyl-1H-1,2,3-triazolo[4,5-d]-pyridazine (1) in three ways, depending on the nature of the reagent. One is substitution of the methylsulfonyl group in 1 by the reagent. The second one is addition of the reagent to the 4,5-double bond in 1. The third one is the addition of the reagent, followed by ring fission of the pyridazine moiety. Thus, the reaction of 1 with sodium methoxide resulted in substitution of the methylsulfonyl group, giving 7-methoxy-1-phenyl-1H-1,2,3-triazolo[4,5-d]pyridazine (2). The addition was found to proceed in the reaction with alkylmagnesium halides and hydrazines, giving the corresponding 4-alkyl-(3a-d) and 4-hydrazino-4,5-dihydro-7-(methylsulfonyl)-1-phenyl-1H-1,2,3-triazolo[4,5-d]-pyridazines (4a, b), respectively. The reaction with primary and cyclic amines resulted in ring fission, giving the corresponding 4-(alkyliminomethyl)-(5b, c) and 4-[di(cyclic amino)methyl]-5-(methyIsulfonylmethyl)-1-phenyl-1H-1,2,3-triazoles (6d-f), respectively. On the other hand, the reaction of 7-chloro-1-phenyl-1H-1,2,3-triazolo[4,5-d]pyridazine (7) with sodium methoxide, hydrazine, and amines resulted in the substitution of the chlorine atom, giving 2, 7-hydrazino-(11), and 7-alkylamino-1-phenyl-1H-1,2,3-triazolo[4,5-d]pyridazines (12a-g), respectively, but neither addition nor ring fission was observed.

• 社団法人日本薬学会の論文
• 1987-02-25

著者

• 大石 悦男

  Division Of Environmental Health Sciences Graduate School Of Nutritional & Environmental Science

• 大石 悦男

  Shizuoka College of Pharmacy

• 山田 晶哉

  Shizuoka College of Pharmacy

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 林 英作

  School Of Pharmaceutical Sciences University Of Shizuoka

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