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 ß-keto esters, ß-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.

Selective Synthesis of N-[1,3,5]Triazinyl-α-Ketoamides and N-[1,3,5]Triazinyl-Amides from the Reactions of 2-Amine-[1,3,5]Triazines with Ketones.

In this study, we report a selective approach for synthesizing N-([1,3,5]triazine-2-yl) α-ketoamides and N-([1,3,5]triazine-2-yl) amides from ketones with 2-amino[1,3,5]triazines through oxidation and oxidative C-C bond cleavage reaction, respectively. The transformation proceeds under mild conditions, provides good functional group tolerance and chemoselectivity, and will serve as a valuable tool for the synthesis of bioactive products.

Diversity-oriented synthesis of imidazo[1,2-a][1,3,5]triazine derivatives from 2-amine-[1,3,5]triazines with ketones.

An I2-mediated annulation of 2-amino[1,3,5]triazines and ketones for the synthesis of imidazo[1,2-a][1,3,5]triazines is presented. Electron rich, or electron poor acetophenone and heterocycle ketones, as well as propiophenone, are functionalized with 2-amino-[1,3,5]triazines. Another class of imidazo[1,2-a][1,3,5]triazines tethered with an additional 1,2-dicarbonyl motif through the combination of annulation and C-H functionalization were obtained instead by changing the reaction conditions. The new methods are practically straightforward and applicable on a gram scale.