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. 2025 Jul 18;90(28):9885-9891.
doi: 10.1021/acs.joc.5c00881. Epub 2025 Jul 8.

Synthesis of 2-Azaanthraquinones from 1,4-Oxazinone Precursors

L C Thompson  1 , Jonathan R Scheerer  1
Affiliations

Synthesis of 2-Azaanthraquinones from 1,4-Oxazinone Precursors

L C Thompson et al. J Org Chem. .

Abstract

The synthesis of 2-azaanthraquinone structures from 1,4-oxazinone precursors is described. A new method for the synthesis of 1,4-oxazinones is also reported. The key discovery is the reaction of oxazinone and quinone starting materials through a tandem cycloaddition/cycloreversion sequence and in situ oxidation to deliver azaquinone products. Insights into the reactivity and selectivity of oxazinone precursors, as well as the description of new biologically active 2-azaanthraquinones further supplement this study.

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Figures

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1
2-Azaanthraquinone parent structure and derivatives.
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1. Proposed Construction of 2-Azaanthraquinone Structures from Oxazinone Precursors
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2. Synthesis of Oxazinone Precursors
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3. Synthesis of 2-AAQs from Oxazinone and Naphthoquinone Precursors
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Proposed synthesis of IQQ intermediate en route to annulated AAQ products.
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4. Formation of Isoquinolinequinone (IQQ) and Annulation to 2-AAQ Products
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