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Synthesis of 2-Aryl-3-(organoselanyl)-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines Promoted by N-Fluorobenzenesulfonimide (NFSI)

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An approach has been developed for the direct synthesis of various selenium-functionalized benzo[4,5]imidazo[2,1- b ][1,3]thiazine derivatives via the electrophilic cyclization reaction between 2-(methylthio)-1-(3-arylprop-2-yn-1-yl)-1 H -benzo[ d ]imidazoles and diorganyl diselenides promoted by N -fluorobenzenesulfonimide (NFSI). This strategy is used to construct fused heterocyclic scaffolds based on selenium-functionalized 4 H -benzo[4,5]imidazo[2,1- b ][1,3]thiazines using NFSI as a stable and nonhazardous oxidizing agent in the presence of CH 3 CN at 80 °C. The protocol allowed a broad substrate scope leading to the synthesis of 16 novel selenium-functionalized benzo[4,5]imidazo[2,1- b ][1,3]thiazines in yields of up to 95%. Furthermore, control studies, including 1 H, 19 F, and 77 Se NMR experiments, were conducted to identify intermediates, which contributed to the elucidation of the reaction mechanism.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c01598