It has been demonstrated that bis(2-nitrophenyl)isoxazoles follow chemoselective reduction pathways leading to 2-aminophenyl-4(1H)-quinolinones. In the presence of a ketone or aldehyde, this reactive intermediate undergoes condensation followed by a Mannich-like ring closure leading to highly fluorescent dibenzonapthyridinones. Analogously, bis(2-nitrophenyl)-1,2,4-oxadiazoles follow a pathway leading to fluorescent dibenzoquinazolinones. The products of these reductive heterocyclizations are not only fluorescent, but display solvatochromism. Current work is exploring the reaction scope, and employing TD-DFT to model the solvent dependent photophysical properties of these systems.

Methodology affording dibenzonapthyridinones: An experimental and computational study

248th National Meeting (2014)

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