- 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)
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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.
- Yamamoto, Hiroshi,Ohira, Chikara,Aso, Toshiaki,Pfleiderer, Wolfgang
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p. 4115 - 4120
(2007/10/02)
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- REACTIONS OF CREATONE (2-METHYLAMINO-1H-IMIDAZOLE-4,5-DIONE)
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Creatone (3) reversibly gives (3-methylguanidino)-glyoxilic acid (6) and its ethyl ester (7) on heating with water and ethanol, respectively.These ring-opened compounds are important intermediates during the formation of creatone from creatine (1) and various other starting materials.
- Yamamoto, Hiroshi,Takahashi, Toshihiro,Inokawa, Saburo
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p. 1067 - 1070
(2007/10/02)
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- 2-Methylamino-4,5-imidazoledione. A Revised Structure for Creatone, Methylparabanic Acid Imide, and (3-Methylguanidino)glyoxylic Acid
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The previous structures presented for the Hg(OAc)2 oxidation product of creatine, the condensation product of methylguanidine and diethyl oxalate, and the peracid oxidation product of 1-methyl-2-amino-dihydropyrimidines are all replaced by a revised formulation, 2-methylamino-1H-imidazole-4,5-dione on the basis of the pKa values (0.62 and 7.87) and the spectra.The equilibria between this thermodynamically controlled product and the previous formulations are discussed.
- Yamamoto, Hiroshi,Pfleiderer, Wolfgang
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p. 1912 - 1914
(2007/10/02)
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