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.
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ABSTRACT: A convenient and efficient synthesis of 2-arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones was developed via a Rh2(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 N2 as the byproduct, and features a broad substrate scope. A plausible mechanism for this reaction is also discussed.
SUBMITTER: He X
PROVIDER: S-EPMC6640800 | biostudies-literature | 2016 Dec
REPOSITORIES: biostudies-literature
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