Bulletin of the Chemical Society of Japan p. 4115 - 4120 (1987)
Update date:2022-07-30
Topics:
Yamamoto, Hiroshi
Ohira, Chikara
Aso, Toshiaki
Pfleiderer, Wolfgang
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 turns was shown to undergo a facile, Dimroth-type rearrangement under weakly acidic conditions to give creatone, thus proving 4 to be the key intermediate in the formation of creatone from various starting materials.The equilibria among these compounds are discussed.
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