Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds

摘要

Anions of heteroaromatic 1,3-dicarbonyl compounds, such as 4-hydoxy-2-quinolones and 4-hydroxy-coumarins, react in DMF in the presence of potassium carbonate with diaryl disulfides to yield 3-arylsulfenyl derivatives. The arylthiolate anions formed in this reaction can be oxidized by air to yield the starting diaryl disulfides again. Tetraalkylthiuram disulfides react in the same manner to yield 3-dialkylaminothiocarbonylthio derivatives of the title compounds. Oxidation of the arylthioderivatives with hydrogen peroxide in sodium hydroxide solution usually leads to sulfoxides, whereas oxidation with peracetic acid affords sulfones.