Regiospecific Cyclization of4-Alkoxyvinyl Trifluoro[chloro]methyl Ketones with6-Trifluoro[chloro]methyl-2-hydrazine Pyrimidines.A Convenient Method to Obtain Trifluoro[chloro]methylated2-(5-Hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-Pyrazol-l-yl]-pyrimidines

Abstract

The regiospecific synthesis of a novel series of 4trifluoro[chloro]-2-(5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-pyrazol-1-yl]-pyrimidines from the reactions of 4-alkoxy-1,1,1-trifluoro[chloro]-alk-3-en-2-ones with 6-trifluoro[chloro]methyl-2-hydrazine pyrimidines is presented.

Trifluoromethyl β‐Enamino Diketones as Dual Substrates for the Synthesis of 5‐Benzoyl‐6‐(trifluoromethyl)pyrimidines and their Pyrimidin‐4(3H)‐one Analogues

“…It is worth highlighting that products 3–6 bear a methyl sulfanyl (–SMe) moiety, which can easily be oxidized with Oxone® or m ‐chloroperbenzoic acid followed by substitution reactions (e.g., with amines to furnish 2‐aminopyrimidines). Such reactions were proven to be effective in parent compounds previously synthesized by our research group …”

“…Such reactions were proven to be effective in parent compounds previously synthesized by our research group. [34][35][36] At this point, it is important to mention that we could not find any reports regarding the elimination of the -CF 3 group in cyclocondensation reactions. Searching for an explanation for this observation, we found an X-ray study that showed interactions between the fluorine of fluorinated molecules and the sp-carbon of the acetonitrile (C-F•••C≡N).…”

Chemoselective O-Alkylation of 4-(Trifluoromethyl)pyrimidin-2(1H)-ones Using 4-(Iodomethyl)pyrimidines

“…However, no formation of the oxidized product was observed. Taking this into account, we next attempted to use m -CPBA, which is another popular oxidizing agent for such reactions. − The conditions were adapted from previous parent substrates, , and after 16 h (using CHCl 3 at r. t.), sulfone 7 was obtained in 92% yield (Scheme ).…”