Directed ortho-Lithiation on Solid Phase.
Resin-bound 1-hydroxyimidazole, obtained by alkylation of the sodium salt of 1-hydroxyimidazole with chloromethyl polystyrene, was lithiated at C-2 with n-butyllithium. Subsequent treatment with carbon, halogen, or sulfur electrophiles followed by detachment from the solid support by heating with trifluoracetic acid at 100 degrees C for 20 h gave 2-substituted 1-hydroxyimidazoles in 52-93% yields.
Havez
Sophie
S
Medicinal Chemistry Research, H. Lundbeck A/S, Ottiliavej 9, DK-2500 Valby, Denmark.
Begtrup
Mikael
M
Vedsø
Per
P
Andersen
Kim
K
Ruhland
Thomas
T