A practical and efficient protocol toward fully substituted isothiazolones through Selectfluor-mediated intramolecular oxidative annulation of α-carbamoyl ketene dithioacetals has been developed in the presence of H 2 O and metal-free conditions. Notably, the experimental results reveal that H 2 O was crucial to the formation of new N−S bonds and the elimination of alkyl group from the sulfur atom. This protocol provides readily prepared substrates and possesses good functional group tolerance, mild reaction conditions, and operational simplicity, which provides potential access to applications in the pharmaceutical chemistry.
A straightforward copper‐catalyzed aerobic cyclocondensation reaction of α‐acyl ketene dithioacetals with ammonium acetate and methanol was developed for synthesizing highly functionalized pyrimidines. This domino conversion relied on the dual activities of CuCl2, namely Lewis acid and dehydrogenation, which began with single C−S ammonolysis directed by an in situ generated imine, followed by cyclocondensation with aldehyde produced from alcohol and concomitant oxidative dehydrogenation under an oxygen atmosphere. Notably, readily accessible and flexible substrates, common chemical feedstock nitrogen and C1 sources, good functional group tolerance and procedural simplicity exhibit the efficiency and potential application of the new method.
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