Polyfunctionalisation of imidazole via sequential imidazolyl anion formation

Article abstract of DOI:10.1016/S0040-4020(97)00939-3

A method for achieving the sequential functionalisation of the imidazole ring in the order C-5→C-4→C-2 is described. The chemistry proceeds via the regioselective formation of positionally stable imidazolyl anions which are reacted with electrophiles (aldehydes, alkyl halides, azides, formamides, isocyanates) to afford substituted imidazoles in 31-90% yield.