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Access to Se/S-Containing Heterocycles via Hexafluoroisopropanol-Mediated Tandem Wolff Rearrangement/Cyclization
Yihan Yu1, Xin Ji2, Xingxing Wu3
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China.
Abstract:
Herein, we report a novel and efficient formal [3 + 3] cyclization strategy for the synthesis of 1,3-selenazines. This protocol relies on the hexafluoroisopropanol (HFIP)-mediated Wolff rearrangement of alkynyl diazoalkyl ketones to in situ generate key alkynyl ketene intermediates, which are sequentially trapped by selenoamides via a cascade reaction to furnish the target 1,3-selenazines. Furthermore, the biological evaluation results demonstrated the promising potential of the resulting organoselenium cyclic scaffolds as lead structures for the development of fungicidal agrochemicals.
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