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2-Amino-1-methyl-1H-imidazole-4, 5-dione: Synthesis and the Dimroth Type Rearrangement to Creatone (2-Methyl-amino-1H-imidazole-4, 5-dione)

H Yamamoto, C Ohira, T Aso, W Pfleiderer

文献索引:Yamamoto, Hiroshi; Ohira, Chikara; Aso, Toshiaki; Pfleiderer, Wolfgang Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 11 p. 4115 - 4120

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被引用次数: 7

摘要

Treatment of creatinine with BOC-ON gave 2-t-butoxycarbonylamino-1-methyl-1, 5-dihydro- 4H-imidazol-4-one, which was oxidized with mercury (II) acetate to the corresponding 1H- imidazole-4, 5-dione. Deprotection of the amino group of this dione afforded the title compound 4, which in turn was shown to undergo a facile, Dimroth-type rearrangement under weakly acidic conditions to give creatone, thus proving 4 to be the key intermediate ...