Authors: Carme C. Llopart; Conchita Ferrer; John A. Joule

Source: Canadian Journal of Chemistry, Volume 82, Number 11, November 2004 , pp. 1649-1661(13)

Publisher: NRC Research Press

Abstract:

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.

On a démontré que les 1-arylimidazol-2(1H)-ones, sous l'action de 2 équivalents molaires de n-butyllithium, subissent facilement une réaction de lithiation sur le noyau benzénique, en position ortho par rapport à l'hétérocycle. Les 1-aryl-4,5-dihydroimidazol-2(1H)-ones subissent aussi une métallation sur le substituant aromatique ortho par rapport à l'hétérocycle, mais la réaction est moins efficace. Les 1-aryl-3-méthylimidazol-2(1H)-ones subissent une réaction de lithiation sur le noyau hétérocyclique avant de procéder à une lithiation sur le noyau benzénique en ortho de l'hétérocycle. On n'a pas observé d'effet d'orientation vers la position ortho avec les 1-aryl-4,5-dihydro-3-méthylimidazol-2(1H)-ones.Mots clés : lithiation en ortho, urées pour des métallations orientées en ortho, 1-arylimidazol-2-ones, 1-arylimidazolidin-2-ones.[Traduit par la Rédaction]

Document Type: Research article

Publication date: 2004-11-01

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