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We described herein a concise synthesis of 3′,4′-diaminoflavone 10. This new, three-step synthetic approach is more efficient than the conventional seven-step synthetic method. The route is shortened significantly by introducing the amino moieties early and eliminating the need for nitro group reduction. The other two analogues, 5,7-dihydroxy-3′,4′-diaminoflavone 11 and 5,7-dimethoxy-3′,4′-diaminoflavone 12, were also synthesized similarly. The above three compounds, along with flavone, were evaluated for their antioxidant and UVB-protection abilities on zebrafish larvae. The data showed that compound 10 exhibited the best result, with −102.3% of ROS-scavenging rate.

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Copper-Mediated Trimethylsilyl Azide in Amination of Bromoflavonoids to Synthesize Unique Aminoflavonoids. -The synthesis of aminoflavonoids from the corresponding bromoflavones and bromoflavanols, respectively is studied. Surprisingly, the fluoride group in (VII) is aminated too. Compared to dibromoflavone (V), dibromoflavanols (IX) give only mono amination products (X). -(SHIH*, T.-L.; CHOU, C.-E.; LIAO, W.-Y.; HSIAO, C.-A.; Tetrahedron 70 (2014) 23, 3657-3664, http://dx.