A General and Facile Route to New Trisubstituted Purin-8-ones

Abstract

A facile general route was developed to synthesise new trisubstituted purin-8-one derivatives starting from cheap and readily available 5-bromouracil. These fused planar heterocycles present key hydrogen bond donating/accepting functionalities, making them interesting scaffolds for binding to biological targets.

Key words

purin-8-ones - fused-ring systems - nucleophilic aromatic substitution - ring-closure - microwave-assisted synthesis

References

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9

The major by-product of the reaction proved to be the monochloro-product coming from the substitution at the most reactive position 4. It can be recovered during the purification and reused.

13

LCMS technique suggested that an acyl chloride intermediate was formed. Moreover, the ¹H NMR of this intermediate showed a split of the signal corresponding to the CH₂ of the 5-benzylamino functionality, suggesting that the acyl chloride is fixed on this amino substituent.