Title

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

Authors

Cameron Iverson

Document Type

Article

Publication Date

2002

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.

Advisor

T. Otsuki

Department

chem

Support

Support provided by:American Chemical Society-PRF Grant



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