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
Index: Yamamoto, Hiroshi; Ohira, Chikara; Aso, Toshiaki; Pfleiderer, Wolfgang Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 11 p. 4115 - 4120
Full Text: HTML
Citation Number: 7
Abstract
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 ...
Related Articles:
[Lee, Yong-Gyun; Yoon, Jin-Hwan; Kim, Jong-Sik; Song, Ju-Hyun; Kim, Yun-Young; Jung, Dai-Il; Hahn, Jung-Tai Asian Journal of Chemistry, 2012 , vol. 24, # 1 p. 129 - 132]
[Poje, M.; Palkovic, A. Tetrahedron Letters, 1985 , vol. 26, # 26 p. 3173 - 3176]
[Matsui, Masaki; Kamiya, Kazusaki; Shibata, Katsuyoshi; Muramatsu, Hiroshige Journal of Organic Chemistry, 1990 , vol. 55, # 4 p. 1396 - 1399]