Divergent Synthesis of α‑(1,3,5-Triazinylthio)-ketones and Thiazolo[3,2‑a][1,3,5]triazines from 1,3-Dicarbonyl compounds or Chalcones with 1,3,5-Triazine-2-thiols

An efficient synthesis of α-(1,3,5-triazinylthio)-ketones from 1,3-dicarbonyl compounds with 1,3,5-triazine-2-thiols has been developed. The reaction proceeds through the C–C bond cleavage and C–S bond reconstruction of 1,3-dicarbonyl compounds, and β-keto esters, β-keto amides, and 1,3-diones were tolerated. In addition, the annulation of 1,3,5-triazine-2-thiols with chalcones has been achieved for the synthesis of thiazolo­[3,2-a]­[1,3,5]­triazines. The method occurred in moderate to good yields and tolerated chalcone with a broad functional group.