Synthesis of β-chloro(trifluoromethyl)acroleins and a specific reaction towards β-aminothiols

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

“…Condensation of o-aminothiophenol, with the enones 179 (or 180 or 181) provided the corresponding benzothiazepines 182a-c in good yields. In the carbohydrate series, the 1,5-benzothiazepines 182c was obtained as an epimeric mixture (D-xylo/L-arabino in a 85 : 15 ratio), indicating that a further C-4 epimerisation had occurred during the formation of the heterocycle [44][45][46][47] (Scheme 36).…”

“…Therefore, upon heating the benzothiazepine 182a to 120 ∘ C, an efficient extrusion of sulfur atom for the benzothiazepine with the aromatic substituent was observed and gave 3-fluoro-2-(4-fluorophenyl)-4-(perfluorobutyl)quinoline 394a in 80% yield [44][45][46][47] (Scheme 71).…”

“…The proton spectra (DMSO-6 ) of (E)-4,4 -methylenebis(2-((E)-4-phenyl-2,3-dihydrobenzo [1,5]thiazepin-2-yl)phenol) 114a and bis(3-phenyl-7-((E)-4-phenyl-2,3-dihydrobenzo [1,5] [44][45][46][47].…”

A new route to 5-trifluoromethyl-2,3-dihydro-1,4-diazepine and 2-trifluoromethylbenzimidazole

“…As a result, in recent years, considerable efforts have been devoted to the development of methodologies for the preparation of fluorine-containing compounds [3][4][5][6][7]. ␣,b-Unsaturated ketones substituted with a trifluoromethyl group represent interesting building blocks for such syntheses.…”

Efficient and General One-pot Synthesis of β-Chloro-β-trifluoromethylated Enones from 3,3,3-Trifluoropropyne

“…[1][2][3] Especially, β-chloro-β-trifluoromethylated enones are very useful building blocks to provide trifluoromethyl substituted heterocycles such as pyrazoles, isoxazoles and pyrimidines. [4][5][6][7] Several methods for the preparation of β-chloro-β-trifluoromethylated enones have been reported in the previous literatures, 6,[8][9] but the previous methods have some drawbacks such as formation of regioisomers, lack of generalization and low yield preparation. Eguchi et al reported that addition of 1,1,1-trichloro-2,2,2-trifluoroethane to carbon-carbon double bond of trimethylsilyl enol ethers in the presence of copper(I) chloride, followed by dehydrochlorination with triethylamine, afforded β-chloro-β-trifluoromethylated enones in moderate yields.…”