115012-02-7Relevant articles and documents
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)
Yamamoto, Hiroshi,Ohira, Chikara,Aso, Toshiaki,Pfleiderer, Wolfgang
, p. 4115 - 4120 (1987)
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.