Environmentally friendly and efficient: iron-mediated reduction of 3-methyl-5-aryl-1,2,4-oxadiazoles to benzamidines

A new synthetic method is described for the mild and selective reduction of 3-methyl-5-aryl-1,2,4-oxadiazoles to amidines employing iron powder in aqueous medium. Its application is demonstrated in the synthesis of 1, a potent and selective urokinase-type plasminogen activator (uPA) inhibitor.