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Synthesis 1995; 1995(11): 1365-1367
DOI: 10.1055/s-1995-4118
short paper
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Synthesis of 5-Substituted Methyl 1-Hydroxyimidazole-4-carboxylates and 5-Substituted Methyl 1-Aminoimidazole-4-carboxylates Using 3-Bromo-2-isocyanoacrylates (BICA)

Masaki Yamada, Toshio Fukui, Ken-ichi Nunami*
  • *Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd., 16-89 Kashima-3-chome, Yodogawa-ku, Osaka 532, Japan, Fax +81(6)3002977
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Publication Date:
31 December 2000 (online)

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A novel synthesis for the title compounds 2 and 3 by the reaction of 3-substituted methyl-3-bromo-2-isocyanoacrylates (BICA) 1 with benzyloxyamine and tert-butyl carbazate, respectively, in the presence of a base was developed.

1-hydroxyimidazole - 1-aminoimidazole - 3-bromo-2-isocyanoacrylate - 1,4,5-trisubstituted imidazole - isonitrile