Reaction of 2-bromo-3-methoxy-1, 4-napthoquinone with amines.
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The synthesis of aminoquinones have been of extreme interest due to their wide spectrum of biological effects including antifungal, antibacterial, and anticancer activities. In order to understand the mechanistic details of their biological effects, we systematically study the synthesis of aminoquinones from simple quinones and amines. In the dark reaction of 2-bromo-3-methoxy-1, 4-napthoquinone with a variety of alkylamines, 2-alkylamino-3-bromo-1, 4-napthoquinones are synthesized in high yields. Interestingly, some of the 2-alkylamino-3-bromo-1, 4-napthoquinones were found to afford 2-amino-3-bromo-1, 4-napthoquinone via the dealkylation reaction under irradiation. The rate of dealkylation is dependent upon the nature of alkyl substituents