4-Trifluoroacetyl-2-phenyloxazol-5-one: Versatile Template for Synthesis of Trifluoromethyl-Substituted Heterocycles

Synthesis of 3‐Aminopyrido[2,1‐a]isoquinolin‐4‐one Derivatives via Condensation of Azlactones with 1‐Alkyl‐3,4‐dihydroisoquinolines

“…[22a] Compound 11 was synthesized from hippuric acid and trifluoroacetic anhydride. [23] Isoquinolines 18 a-e, 19 a, 20 a were synthesized by threecomponent condensation of substituted arenes 12 a-e with nitriles 13-15 and 2-methylpropanal in H 2 SO 4 , [24] and compound 21 a was obtained by the Ritter reaction of carbinol 16 with MeCN in H 2 SO 4 . [25] Compound 22 was prepared by the Bischler-Napieralski reaction [26] from amide 17 and POCl 3 .…”

“…Compound 10 was prepared by reacting sodium hippurate with acetic anhydride [22a] . Compound 11 was synthesized from hippuric acid and trifluoroacetic anhydride [23] …”

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

“…Different synthetic routes have been developed to synthesize trifluoromethyl-β-dicarbonyls (Figure 3). These include: i) the most classical approach involving Claisen condensation of ketones and ethyl 2,2,2-trifluoroacetate under basic conditions, [56,57] or by the condensation of 1,1,1-trifluoroacetone and the corresponding perfluoroalkylesters, [58] ii) Claisen-type condensation of lithium enolates of acetyltrialkylsilanes with the fluorinated carboxylic acid derivatives, [59] iii) Claisen condensation of acetal-functionalized ketone and perfluoroalkylesters in the presence of calcium hydride followed by complexation and treatment with disodium ethylenediaminetetraacetate, [60] iv) acylation of 1,1-dimethoxy-1-(thien-2-yl)propane with trifluoroacetic anhydride in pyridine, [61] v) acylation of cyclohexane-1,3-diones by N-perfluoroacylimidazoles which in turn generated in situ from imidazole and trifluoroacetic anhydride, [62] vi) reaction of N-benzoylglycine and trifluoroacetic anhydride, [63] and vii) reaction of enamines with hexafluoropropene oxide in anhydrous THF, [64] etc.…”

Combining Donor Strength and Oxidative Stability in Scorpionates: A Strongly Donating Fluorinated Mesoionic Tris(imidazol-5-ylidene)borate Ligand

“…The resulting crude product was recrystallized from 15% ethyl acetate in hexanes to obtain off-white crystals (5.1 g, 30% yield). The spectral data for this compound matches a previous literature report …”

“…The spectral data for this compound matches a previous literature report. 98 This procedure was based on literature procedures. 73 A 1 L Schlenk flask was charged with 5trifluoromethyl-1-methyl-2-phenyl-1H-imidazole (8.1 g, 36 mmol) and 200 mL of toluene.…”