1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.Key words: ortho-lithation, ureas for directed ortho metalation, 1-arylimidazol-2-ones, 1-arylimidazolidin-2-ones.

6-Ethyl-2,3-dihydro-1-phenyl-1H-pyrrolizine 19 and 1-(2-aminophenyl)-6-ethyl-2,3-dihydro-1H-pyrrolizine 30 were synthesized starting from the pyrroles 4-acetylpyrrol-2-yl phenyl ketone 13 and 4-acetylpyrrol-2-yl 2-(dimethylaminomethylenamino)phenyl ketone 26, respectively, using vinyltriphenylphosphonium bromide in an intramolecular Wittig reaction for the formation of the second five-membered ring.

Reactions of organo-metal compounds O 0350Lithiation of 1-Arylimidazol-2(1H)-ones and 1-Aryl-4,5-dihydroimidazol-2(1H)-ones. -The title investigation is presented in extension of previously published studies on the utilization of cyclic urea derivatives in directed ortho metalation reactions. Attempted ortho metalation of N-methylated analogous of compound (VII) are mentioned to fail. -(LLOPART, C. C.; FERRER, C.; JOULE*, J. A.; Can.