SYNTHESIS AND RECYCLIZATION REACTIONS OF 4-(O-R-PHENYL)-3-IMIDAZOLINES

1-Hydroxy-4-phenyl-3-imidazoline reacts with butyllithium to give the product of ortho-metallation of the phenyl group. Reactions of this co mpound with electrophiles followed by oxidation afford 4-(o-R-phenyl) derivatives of nitroxyl radicals. When a hydroxyalkyl group is present in the ortho-position, an unusual pathway of the decay of stable nitr oxyl radicals of the imidazoline series has been observed due to the e xistence of a spirobicyclic tautomer. The reaction of the o-metallated derivative with CS2 leads to a profound transformation of the imidazo line ring and to the formation of isoindolethione. Fast recyclization into isoquinolines occurs in the case of the 4-(o-benzoyl)phenyl deriv ative of 3-imidazoline. The product of o-metallation reacts with methy l nitrate to yield the 4-(o-hydroxy)phenyl derivative (a potential par amagnetic chelate-forming reagent) and the o-nitro derivative, the sta rting material for further chemical transformations.