The oxidation of acetone (I) with butyl nitrite (II) with a catalytic amount of HCl gives methylglyoxal 1-oxime (III), which is then condensed with aminoguanidine (IV) in hot water acidified with HCl.
The synthesis of [14C]-mitoguazone has been reported: The methylation of [14C]-labeled potassium acetate (I) with dimethyl sulfate in HMPT gives the corresponding ester (II), which by reaction with the sodium salt of dimethylsulfoxide (III) in DMSO affords the hemithioketal (IV). Finally, this compound is condensed with aminoguanidine (V) in DMSO/water.