American Chemical Society
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Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles

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journal contribution
posted on 2020-04-06, 10:29 authored by Jin-Yu Chen, Manikandan Selvaraju, Yen-Tzu Lin, Sandip Dhole, Chih-Yu Lin, Chung-Ming Sun
Two new classes of heteroarene-fused [1,2,4]­thiadiazole and [1,2,4]­selenadiazole are synthesized through the iodine-mediated [3 + 2] oxidative cyclization of 2-aminoheteroarenes and isothiocyanates/isoselenocyanates. This oxidative [3 + 2] annulation strategy is highly regiospecific to proceed a selective C–N bond formation at the endo-nitrogen of 2-aminoheteroarenes followed by an intramolecular oxidative N–S/N–Se bond formation. It is the first example of an I2-mediated oxidative nitrogen–selenium (N–Se) bond formation.