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12.3.1.1.1.2.2 Variation 2: Use of Hydroxylamine in Place of Ammonia or Amines; 1-Hydroxyimidazoles and 1-Hydroxyimidazole 3-Oxides

DOI: 10.1055/sos-SD-012-00398

Grimmett, M. R.Science of Synthesis, (200212335.

Replacement of ammonia or the primary amine by hydroxylamine in these reaction types allows preparation of 1-hydroxy-1H-imidazole 3-oxides 26 (Scheme 13).[‌44‌] Subsequent hydrogenation with palladium on carbon in aqueous hydrochloric acid, or reduction with titanium(III) chloride in aqueous solution at room temperature gives 1-hydroxyimidazoles.[‌45‌] Note that imidazole oxides have been known to decompose violently when heated.[‌46‌]

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