Reactions of 1-(2-Acetoxyethoxy)methyl-5-amino-4-cyanoimidazole with Isothiocyanates

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概要

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• The reactions of 1-(2-acetoxyethoxy)methyl-5-amino-4-cyanoimidazole (5) with isothiocyanates afforded 3-(2-acetoxyethoxy)methyl-5-(substituted amino)-7-(N-substituted thiocarbamoyl)-iminoimidazo[4,5-d][1,3]thiazine (6a-c) at 50℃ in dimethylformamide. At more elevated temperature, for example, in refluxing pyridine, compound 5 reacted with methyl isothiocyanate to give 3-2(acetoxyethoxy)methyl-5-methylamino-7-(N-methylthiocarbamoyl)iminoimidazo[4,5-d][1,3]-thiazine (6b) and 9-(2-acetoxyethoxy)methyl-1-methyl-6-imino-2-thioxopurine (7b).On the other hand, when carbon disulfide was used in place of isothiocyanates, the reaction afforded 3-(2-acetoxyethoxy)methyl-7-imino-5-thioxoimidaxo]4,5-d][1,3]thiazine (8) in refluxing pyridine.Under alkaline conditions, 6 and 8 were found to be rearranged to 2-(substituted amino)-9-(2-hydroxyethoxy)methyl-6-thioxopurine (10) and 2,6-dithioxo-9-(2-hydroxyethoxy)methylpurine (9), respectively.

• 社団法人日本薬学会の論文
• 1988-04-25

著者

• 松本 広淳

  Research Laboratory, Minophagen Pharmaceutical Co.,

• 森 武雄

  Research Laboratory, Minophagen Pharmaceutical Co.,

• 水野 義久

  School Of Pharmaceutical Sciences Kitasato University

• 水野 義久

  北海道大学 薬

• 山田 敬子

  Research Laboratory Minophagen Pharmaceutical Co.

• 金子 千里

  Research Laboratory, Minophagen Pharmaceutical Co.,

• 竹内 惟雄

  Research Laboratory, Minophagen Pharmaceutical Co.,

• 水野 義久

  Research Laboratory, Minophagen Pharmaceutical Co.,

• 森 武雄

  Research Laboratory Minophagen Pharmaceutical Co.

• 松本 広淳

  Research Laboratory Minophagen Pharmaceutical Co.

• 竹内 惟雄

  Research Laboratory Minophagen Pharmaceutical Co.

• 金子 千里

  Research Laboratory Minophagen Pharmaceutical Co.

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