Chemoselective reactions of 2,3-dichloro-1,4-naphthoquinone

摘要

The reaction of 2,3-dichloro-1,4-naphthoquinone with alkoxides, primary amines, and phenols was shown to proceed chemoselectively rather to the corresponding 2-substituted 3-chloronaphthoquinones or 2,3-disubstituted quinones than to brazanquinone derivatives. Difunctional reagents like mercaptobenzimidazole, methyl urea, or guanidine lead to the corresponding heterocyclic system. The chemoselectivity of these reactions was found to be critically dependent on the reagents and reaction conditions used. These reaction parameters can thus be used to govern the synthesis of distinct compounds. [References: 26]