Sulfenylation of Heterocyclic 1,3-Dicarbonyl Systems:4-Hydroxy-2-pyrones, 6-Hydroxy-4-pyrimidones, 4-Hydroxy-2-pyridones, 4-Hydroxy-6-pyridazinones, and 5-Hydroxy-3-pyrazolones

摘要

Anions of enolized heteroaromatic 1,3-dicarbonyl systems, such as the title compounds 1,9,14, and 19, react in dimethylformamide in the presence of potassium carbonate with diaryl disulfides 2 to yield arylsurfenyl derivatives (3,10,15,20). The arylthiolate anions 4 formed in this reaction can be oxidized by air to yield the starting disulfides 2 again. etrakklkylthiuram disulfidgs 7 react in the same manner to yield diakylaminothiocarbonylthio derivatives (8,13,18)of the title compounds. Oxidaztion of the srysulfenyl derivatives with hydrogen peroxide in sodium hydroxide solution usually leads to sulfoxides (5,11,16), wherea oxidation ith peracetic acid affords sulfones(6,12,17).