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

**Authors:** L. C. Thompson, Jonathan R. Scheerer

PMC · DOI: 10.1021/acs.joc.5c00881 · The Journal of Organic Chemistry · 2025-07-08

## TL;DR

This paper describes a new method to synthesize 2-azaanthraquinones from 1,4-oxazinone precursors using a tandem chemical reaction.

## Contribution

A new synthetic method for 2-azaanthraquinones using a tandem cycloaddition/cycloreversion sequence is introduced.

## Key findings

- A tandem cycloaddition/cycloreversion sequence with in situ oxidation produces azaquinone products.
- New biologically active 2-azaanthraquinones were synthesized and characterized.
- The reactivity and selectivity of oxazinone precursors were studied in detail.

## 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.

## Linked entities

- **Chemicals:** 1,4-oxazinone (PubChem CID 21264915), quinone (PubChem CID 4650)

## Full-text entities

- **Chemicals:** 1,4-oxazinone (-), quinone (MESH:C004532)

## Full text

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## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12281559/full.md

## References

43 references — full list in the complete paper: https://tomesphere.com/paper/PMC12281559/full.md

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Source: https://tomesphere.com/paper/PMC12281559