64196-43-6

Upstream product

• 78396-00-6 2-aminochalcone 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 98-86-2 acetophenone 
• 205756-49-6 1,1,1-trifluoro-2-hydroxy-2-(2-aminophenyl)ethane 
• 1636-34-6 2,3-diphenyl-2,3-butanediol 
• 17408-17-2 2,2,2-trifluoro-1-(2-nitrophenyl)ethanone 
• 132-60-5 cinchophen 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 98-85-1 1-Phenylethanol 
• 700362-32-9 2,2,2-trifluoro-1-(2-nitrophenyl) ethanol 
• 536-74-3 phenylacetylene 
• 351002-89-6 1-(2-amino-5-phenyl)-2,2,2-trifluoroethanone 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 

Relevant academic research and scientific papers

A Convenient Synthesis of 4-CF3-Quinolines from 1-Trifluoromethyl-prop-2-yne 1-Iminium Salts and Arylamines

A convenient synthesis of 4-trifluoromethyl-quinolines from 1-trifluoromethyl-prop-2-yne 1-iminium triflates and anilines in a one-pot two-step Michael addition/intramolecular cyclization sequence is reported. With ring-substituted anilines, a wide range of 4-CF3-quinolines bearing additional substituents and functional groups in the C-2, C-6, and C-8 positions were prepared, mostly in high yields. Even a 4-CF3-5-Me-quinoline could be obtained. From mono-Boc protected 1,4- and 1,3-phenylenediamine, 2-aryl-substituted 6-amino-4-CF3-quinoline and 7-amino-4-CF3-quinoline, respectively, were prepared. 4-CF3-benzo[h]quinolines were obtained from the mentioned acetylenic iminium salts and 1-naphthylamine. With N-monosubstituted aromatic amines such as N-methylaniline and 1,2,3,4-tetrahydroquinoline, N-substituted 4-CF3-quinolinium salts and pyrrolo[1,2-a:3,4-c']diquinoline derivatives bearing two CF3 substituents could be prepared.

Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines

A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.

Pd-Catalyzed Decarboxylative Cyclization of Trifluoromethyl Vinyl Benzoxazinanones with Sulfur Ylides: Access to Trifluoromethyl Dihydroquinolines

An unprecedented Pd-catalyzed decarboxylative cyclization of 4-trifluoromethyl-4-vinyl benzoxazinanones (4) with sulfur ylides (2) is reported. While the reactions of 4-vinyl/4-CF3 benzoxazinanones (1a/1c) with 2 furnished the 3-vinyl/3-CF3 indolines (3a/3c), via an attack on the C1 carbon of the π-allyl/benzyl zwitterionic intermediates, 4 was converted into 4-trifluoromethyl-dihydroquinolines (5) in good yields via an attack on the C3 carbon of the π-allyl intermediate. The corresponding methyl-substituted analogues afford different products via an attack on the C2 carbon.

Redox-Neutral Decarbonylative Cross-Couplings Coming of Age

Major progress has recently been made in the challenging redox-neutral decarbonylative cross-coupling of carboxylic acids. For example, the use of acid fluorides as effective cross-coupling partners has been found to enable control of the decarbonylation selectivity and facilitates challenging Pd0-catalyzed nucleophilic trifluoromethylation and exogenous base-free Suzuki cross-coupling reactions. In another recent advance, the use of acid chlorides in room temperature difluoromethylation and direct decarbonylative cross-coupling of carboxylic acids allows these classical substrates to be used as aryl electrophiles in cross-coupling reactions. Further challenges that are yet to be addressed in redox-neutral decarbonylative cross-couplings are also briefly summarized.

Molybdenum-Catalyzed Sustainable Friedl?nder Synthesis of Quinolines

Polysubstituted quinolines have been efficiently synthesized from nitroarenes and glycols, as reducing agents, under dioxomolybdenum(VI)-catalysis. Interestingly, the waste reduction byproduct is incorporated into the final heterocycle. This method repres

Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides

While acid fluorides can readily be made from widely available or biomass-feedstock-derived carboxylic acids, their use as functional groups in metal-catalyzed cross-coupling reactions is rare. This report presents the first demonstration of Pd-catalyzed

Synthesis of Quinolines via Iron-Catalyzed Redox Condensation of Alcohols with 2-Nitrobenzyl Methyl Ether/2-Nitrobenzyl Alcohols

An iron-catalyzed redox condensation of 2-nitrobenzyl alcohols, formic acid, and alcohols has been developed, which affords substituted quinolines with carbon dioxide and water as the only side products. With the use of formic acid as a redox moderator to fill the electron gap of the global redox condensation process, the reaction goes smoothly with a smaller amount of alcohol in comparison to previous reports (i.e. 1.2 equiv versus 3.3-4 equiv). The reaction goes equally well when 2-nitrobenzyl methyl ether was used instead of 2-nitrobenzyl alcohol under otherwise identical conditions, shedding a new light on the study of this quinoline synthetic method.

Silver catalyzed synthesis of 4-trifluoromethyl substituted quinolines in water

Herein we report the first silver catalyzed fluorinated quinoline synthesis via a cascade alkyne-ketone-amino coupling/addition/condensation process in water.

Quinoline formation via a modified Combes reaction: Examination of kinetics, substituent effects, and mechanistic pathways

A comprehensive product regioselectlvity and kinetics study of the modified Combes quinoline synthesis shown below has been undertaken: This is the first reported investigation of the Combes condensation employing 19F NMR spectroscopy to monitor intermedi

Zn(II)-mediated alkynylation-cyclization of o-trifluoroacetyl anilines: One-pot synthesis of 4-trifluoromethyl-substituted quinoline derivatives

A novel efficient route to 4-trifluoromethylsubstituted quinoline derivatives through the Zn(II)-mediated alkynylation-cyclization of o-trifluoroacetyl anilines is described.