2-(N-Alkylamino)-1-(trifluoroacetimidoyl)vinyl ketone derivatives as potential reagents in heterocyclic synthesis

Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib

“…Enaminone compounds are highly versatile intermediates in organic synthesis . However, literature surveys show that the application of their fluoroalkylated counterparts remains largely underdeveloped (Scheme b), which could be attributed to the synthesis difficulties. , For instance, trifluoromethylated enaminones can be synthesized from CF 3 CN. However, CF 3 CN is a toxic gas, and the reaction needs to use highly acidic and basic reagents .…”

“…Alternatively, they can be prepared from corresponding diketones. However, regioselectivity could be a problem …”

Dual Role of (NH4)2CO3 Enables Defluorinative Synthesis of β-Fluoroalkylated Aminovinyl Ketones

“…Traditionally, active methylene compounds can react with gaseous trifluoroacetonitrile (CF 3 CN) to give β-trifluoromethylated aminovinyl ketones (Scheme , B, a) . This approach shows a heavy reliance on the use of toxic CF 3 CN, and harsh conditions are generally needed for the desired transformation.…”

Synthesis of 4-(trifluoromethyl)pyrido[4,3-d]pyrimidine derivatives

“…Recently, 14 we have found a method for the prepara tion of 4 amino 3 trifluoroacetimidoyl 3 penten 2 one (8) from chelate 2 and suggested a possibility to use this com pound as a new building block for the construction of CF 3 containing heterocycles (Scheme 2). For instance, the reaction of aminovinyl imine 8 with dimethylform amide dimethyl acetal (DMF DMA) in the ratio 1:1 led to the formation of (trifluoromethyl)pyrimidine 9, whereas the use of the acetal in excess amounts allowed us to syn thesize dimethylaminovinylpyrimidine 10.…”