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    Reaction of 2-Bromo-3-methyl-1,4-naphthoquinone with Amines: A Novel Demethylation Reaction.

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    Author
    Iverson, Cameron
    Issue
    urc_student; urc_student
    Date
    2002-01-01 0:00
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    URI
    https://scholar.oxy.edu/handle/20.500.12711/717
    Abstract
    Due to often-unexpected reactivities, 1,4-naphthoquinone derivatives are utilized as anti-fungal, antibacterial, and potential anticancer pharmaceuticals. Here we study the reactivity of 2-bromo-3-methyl-1,4-naphthoquinone toward primary and secondary amines. n the reaction with primary amines in methanol, contrary to our expectations, demethylation of 2-bromo-3-methyl-1,4-naphthoquinone generates 2-alkylamino-3-bromo-1,4-naphthoquinoneas the major product. Furthermore, secondary amines such as N-ethylmethylamine gave 2-methylamino-3-bromo-1,4-naphthoquinone, presumably as the secondary reaction product. The reaction mechanism is discussed.
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