An
efficient iodine-mediated method is developed for the synthesis
of functionalized 2-(methylthio)-4H-chromen-4-ones
by intramolecular cyclization of easily accessible 1-(2-benzyloxy-aryl)-3,3-bis-methylsulfanyl-propenones.
The synthesized chromen-4-ones turn out to be a key precursor for
various kinds of chemical reactions. Mechanistically, we observed
that iodine-mediated intramolecular cyclization of ketene dithioacetal
proceeded through a radical pathway. 3-Halo-2-(methylthio)-4H-chromen-4-ones were achieved via various two- or one-pot
halogenation approaches.
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