Lithiation of 1-arylimidazol-2 (1 H)-ones and 1-aryl-4, 5-dihydroimidazol-2 (1 H)-ones

CC Llopart, C Ferrer, JA Joule

Index: Llopart, Carme Cantos; Ferrer, Conchita; Joule, John A. Canadian Journal of Chemistry, 2004 , vol. 82, # 11 p. 1649 - 1661

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Citation Number: 15

Abstract

1-Arylimidazol-2 (1 H)-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 (1 H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2 (1 H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found ...