Access to Isoxazoles via Photo-oxygenation of Furan Tethered α-Azidoketones

Photocatalyst-free visible light-enabled direct oxygenation of furan-tethered α-azidoketones was studied. The reaction yielded various products depending on the substituents, with isoxazoles forming as the major products. The findings suggest that singlet oxygen was generated during the reaction and reacted with α-azidoketones in a [4 + 2] fashion to yield endoperoxides, which rearranged in multiple ways to generate isoxazoles. Some of the synthesized isoxazoles were evaluated as α-glucosidase inhibitors, and three of them 5bi, 5bj, and 5bl exhibited good activity with IC₅₀ values of 454.57 ± 29.34, 147.84 ± 2.28, and 272.58 ± 42.06 μM, respectively, when compared with the standard drug acarbose (IC₅₀ = 1224.33 ± 126.72 μM).