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Updated: May 10, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis of a hydrophilic naphthalimidedioxime
Christopher D Grant1, Sung Ok Kang, Benjamin P Hay
1Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37831, USA.
Abstract:
Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.
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