Michael P. Groziak and Hong Ding
Pharmaceutical Discovery Division, SRI International
333 Ravenswood Avenue, Menlo Park, CA, 94025-3493, USA
e-mail: michael.groziak@sri.com
 

ABSTRACT

Regioselective syntheses of 4- and 5-(acylamino)-1-alkylimidazoles bearing an ortho-halogen atom have been developed.  Suitable for use in ortho-directed halogen-metal exchange-mediated ring functionalizations, these compounds are valuable precur-sors to ortho-functionalized versions of biologically active 4- and 5-aminoimidazoles.  To widen the scope of this approach to cover similarly-substituted benzimidazoles and their potentially bioactive nucleosides, the synthesis of halogenated 5- and 6-(acylamino)-benzimidazoles and their ribosides was also explored.