| Abstract: | Regiochemically defined 1-benzyl-4-phosphono-5-carboalkoxyimidazoles were synthesized from the corresponding 4-bromoimidazoles using a tetrakis(triphenylphosphine)palladium(0)-catalyzed coupling reaction with diethyl phosphite. The corresponding Michaelis-Arbusov reaction failed to give a phospho-nylated product. The carbomethoxy moiety was converted to an amino group using a Curtius rearrangement to afford 1-benzyl-4-phosphono-5-amino-imidazoles. Following deprotection and hydrolysis, phos-phonic acid-linked aminoimidazoles were accessed that resemble intermediates formed during purine biosynthesis. |
