2-Amino-1-methyl-1H-imidazole-4,5-dione: Synthesis and the Dimroth type rearrangement to creatone (2-methylamino-1H-imidazole-4,5-dione).

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概要

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• Treatment of creatinine with BOC-ON gave 2-<I>t</I>-butoxycarbonylamino-1-methyl-1,5-dihydro-4<I>H</I>-imidazol-4-one, which was oxidized with mercury(II) acetate to the corresponding 1<I>H</I>-imidazole-4,5-dione. Deprotection of the amino group of this dione afforded the title compound <B>4</B>, which in turn was shown to undergo a facile, Dimroth-type rearrangement under weakly acidic conditions to give creatone, thus proving <B>4</B> to be the key intermediate in the formation of creatone from various starting materials. The equilibria among these compounds are discussed.

• 公益社団法人 日本化学会の論文

著者

• Ohira Chikara

  Department of Chemistry, Faculty of Science, Okayama University

関連論文

• 2-Amino-1-methyl-1H-imidazole-4,5-dione: Synthesis and the Dimroth type rearrangement to creatone (2-methylamino-1H-imidazole-4,5-dione).

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