45376-79-2

Upstream product

• 288-32-4 1H-imidazole 
• 35321-46-1 1-hydroxy-1H-imidazole-3-oxide 

Downstream Products

• 131468-90-1 1-Methoxy-1H-imidazole 
• 121779-19-9 1-(benzyloxy)imidazole 
• 126355-38-2 1-trityloxy-1H-imidazole 
• 126355-39-3 1-phenoxy-1H-imidazole 
• 131468-91-2 1-Phenethyloxy-1H-imidazole 
• 126355-47-3 allyloxyimidazole 
• 126355-49-5 1-(2,4-Dichloro-benzyloxy)-1H-imidazole 
• 548767-52-8 Morpholine-4-carboxylic acid imidazol-1-yl ester 
• 548765-40-8 methyl-phenyl-carbamic acid imidazol-1-yl ester 

Relevant academic research and scientific papers

Synthesis of 2-Substituted 1-Hydroxyhnidazoles through Directed Lithiation

Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon, halogen, silicon, or sulfur substituents at the 2-position. Subsequent debenzylation afforded 2-substituted 1-hydroxyimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

Preparation of N-Hydroxyazoles by Oxidation of Azoles

Azoles without N-substituents are oxidized with per-acids or perborate to the corresponding N-hydroxy substituted azoles. 1,2,4-Triazole and tetrazole produce two isomers separated through their O-benzyl derivatives.Imidazole and 1,2,3- and 1,2,4-triazole can be di-oxygenated in low yields.N-Hydroxypyrazole is deoxygenated by per-acid.