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 alpha-(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 beta-keto esters, beta-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.

Automated summary

An efficient method for the synthesis of alpha-(1,3,5-triazinylthio)-ketones from 1,3-dicarbonyl compounds with 1,3,5-triazine-2-thiols has been developed. The reaction involves C-C bond cleavage and C-S bond reconstruction of 1,3-dicarbonyl compounds, and can tolerate beta-keto esters, beta-keto amides, and 1,3-diones. 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 in moderate to good yields, and with a broad functional group tolerance.