Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation

Synthesis of 2-Substituted 1-Hydroxyimidazoles 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...

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Veröffentlicht in:Journal of organic chemistry 1998-01, Vol.63 (1), p.12-16
Hauptverfasser: Eriksen, Birgitte Langer, Vedsø, Per, Morel, Sandrine, Begtrup, Mikael
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container_title Journal of organic chemistry
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creator Eriksen, Birgitte Langer
Vedsø, Per
Morel, Sandrine
Begtrup, Mikael
description 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.
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title Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation
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