Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds

Abstract

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 disul®des to yield 3-arylsulfenyl derivatives. The arylthiolate anions formed in this reaction can be oxidized by air to yield the starting diaryl disul®des again. Tetraalkylthiuram disul®des 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.

Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

“…On the other hand, tetraalkylthiuram disulfides 131 reacted with 4-hydroxycoumarin 1 to yield of 3-dimethylaminothiocarbonylthio-4-hydroxycoumarin 132 (Schnell and Kappe, 1999) (Scheme 69). Scheme 69.…”