| Abstract: | The imidazolinone herbicides were prepared from reaction of an α- methylvaline fragment with an o-dicarboxylic acid. Early syntheses were completed through an imide amide intermediate, such as I or XV , followed by further cyclization to 2,5-diones III or XXI . Reaction of these diones with nucleophiles led to imidazolinones IV and V . The significant and interesting activity of these compounds led to new and versatile methods of synthesis, including resolution of the α-methylvaline fragments, development of a metallation-carboxylation route, a one-step picoline to imidazolinone route, and several pyridine and fused-ring pyridine syntheses. |
