Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh₂(OAc)₄-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates

摘要

A convenient and efficient synthesis of 2-arylimino-6,7-dihydrobenzo[d ][1,3]oxathiol-4(5H )-ones was developed via a Rh_(2)(OAc)_(4)-catalyzed reaction of cyclic 2-diazo-1,3-diketones and aryl isothiocyanates in acetone at 60 °C. This reaction uses readily available stable cyclic 2-diazo-1,3-diketones as a starting material and generates the desired products in good to excellent yields (78–93%). The reaction proceeds under mild reaction conditions, produces only N_(2) as the byproduct, and features a broad substrate scope. A plausible mechanism for this reaction is also discussed.