DIRECTED ORTHO-LITHIATION ON SOLID-PHASE

Resin-bound 1-hydroxyimidazole, obtained by alkylation of the sodium s alt 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 suppor t by heating with trifluoracetic acid at 100 degrees C for 20 h gave 2 -substituted 1-hydroxyimidazoles in 52-93% yields.