Title

Photochemical Reaction of 2-Alkylamino-1,4-naphthoquinones: A Novel Dealkylation.

Document Type

Article

Publication Date

2003

Abstract

Naphthoquinone derivatives find vast applications both in pharmaceutical and agricultural sciences, for example, as antibacterials, antifungals, antitumors and herbicides. Here we investigate the reactivity of 2-alkylamino-3-bromo-1,4-naphthoquinones under illumination. All 2-alkylamino-3-bromo-1,4-naphthoquinones we studied were found to yield 2-amino-3-bromo-1,4-naphthoquinone. The alkyl group in the alkylamino group and the solvent influence the reactivity of 2-alkylamino-3-bromo-1,4-naphthoquinone and the yield. The alkyamino groups we used were n-propylamino, isopropylamino, cyclopropylamino, n-butylamino, sec-butylamino, and tert-butylamino groups; the solvents used were methylene chloride, chloroform, and benzene. 2-Bromo-3- isopropylamino-1,4-naphthoquinone in methylene chloride, for example, was converted into 2-amino-3-bromo-1,4-naphthoquinone in a high yield (85%) upon illumination. On the other hand, 2-bromo-3-tert-butyl-1,4-naphthoquinone yielded 2-amino-3-bromo-1,4-naphthoquinone only in poor yield. We believe hydrogen abstraction by excited quinone is the critical step in the dealkylation reaction.

Advisor

T. Otsuki

Department

chem

Support

Support provided by:National Science Foundation - Research Experience for Undergraduates

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