Synthesis of potential inhibitors of GTP-cyclohydrolase I: an efficient synthesis of 8-substituted 7-deazaguanines

Abstract

A novel two step synthesis of 8-substituted 7-deazaguanines is developed and involves the regioselective alkylation of pyrimidinones 1a and 1b with nitrosoalkenes derived from α-halo oximes followed by transoximation to give the 7-deazaguanines 6a–d in 41–65% overall yield