Fluorinated Quinolines: Synthesis, Properties and Applications

Lipunova, G. N.; Носова, Э. В.; Charushin, Valery N.

doi:10.1007/978-3-319-04435-4_2

Cited by 3 publications

(3 citation statements)

References 121 publications

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“…Notably, thermal cyclization of 15 occurs regioselectively at the 2-rather than the 8-position of the naphthalene ring system. The constitution of benzo[h] quinolines 14 was derived from the 1 H and 13 C NMR spectra including a comparison with 4-CF 3 -quinolines 2; the most characteristic signal is provided by the deshielded proton 9-H (for 15 a: δ = 9.49 ppm, 3 J H,H = 8.0 Hz).…”

Section: Resultsmentioning

confidence: 99%

“…Prepared from salt 1 b (R = 4-chlorophenyl) (1.02 g, 2.50 mmol) and 2nitroaniline (375 mg, 2.50 mmol) in CH 3 CN (6 mL) according to GP1; heating at 87°C for 67 h. When the warm reaction solution was allowed to assume room temperature, a major part of the product precipitated as colorless needle-shaped crystals, which were isolated by filtration and washed with cold CH 3…”

Section: -(4-chlorophenyl)-8-nitro-4-(trifluoromethyl)quinoline (2 R)mentioning

confidence: 99%

“…Consequently, a variety of synthetic strategies -time-honored named and unnamed reactions -have been developed, which provide access to a wide array of (regioselectively) substituted quinolines. [1,2] More recently, syntheses and applications of fluoro-and trifluoromethyl-substituted quinolines have attracted attention, [3] because incorporation of fluorine atoms can alter physical and (physico)chemical properties and bioactivities of a compound. [4] The structures of two fluorine-containing, pharmaceutically active quinoline derivatives are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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A convenient synthesis of 4-trifluoromethyl-quinolines from 1trifluoromethyl-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-CF 3 -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-CF 3 -5-Me-quinoline could be obtained. From mono-Boc protected 1,4-and 1,3-phenylenediamine, 2-aryl-substituted 6-amino-4-CF 3 -quinoline and 7-amino-4-CF 3 -quinoline, respectively, were prepared. 4-CF 3 -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-CF 3 -quinolinium salts and pyrrolo[1,2-a:3,4-c']diquinoline derivatives bearing two CF 3 substituents could be prepared.

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Section: Resultsmentioning

confidence: 99%

Section: -(4-chlorophenyl)-8-nitro-4-(trifluoromethyl)quinoline (2 R)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks

2021

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Organofluorine chemistry: promising growth areas and challenges

Politanskaya¹,

Селиванова²,

Panteleeva³

et al. 2019

Russ. Chem. Rev.

147

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Currently, the chemistry of organofluorine compounds is a leading and rapidly developing area of organic chemistry. Fluorine present in a molecule largely determines its specific chemical and biological properties. This thematic issue covers the trends of organofluorine chemistry that have been actively developed in Russia the last 15 – 20 years. The review describes nucleophilic substitution and heterocyclization reactions involving fluorinated arenes and quinones and skeletal cationoid rearrangements in the polyfluoroarene series. The transformations involving CF3-substituted carbocations and radical cations are considered. Heterocyclization and oxidative addition reactions of trifluoroacetamide derivatives and transformations of the organic moiety in polyfluorinated organoboranes and borates with retention of the carbon – boron bond are discussed. Particular attention is devoted to catalytic olefination using freons as an efficient synthetic route to fluorinated compounds. The application of unsymmetrical fluorine-containing N-heterocyclic carbene ligands as catalysts for olefin metathesis is demonstrated. A variety of classes of organofluorine compounds are considered, in particular, polyfluorinated arenes and 1,2-diaminobenzenes, 1-halo-2-trifluoroacetylacetylenes, α-fluoronitro compounds, fluorinated heterocycles, 2-hydrazinylidene-1,3-dicarbonyl derivatives, imines and silanes. The potential practical applications of organofluorine compounds in fundamental organic chemistry, materials science and biomedicine are outlined. The bibliography includes 1019 references.

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Fluorinated Quinolines: Synthesis, Properties and Applications

Cited by 3 publications

References 121 publications

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

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

Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks

Organofluorine chemistry: promising growth areas and challenges

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Fluorinated Quinolines: Synthesis, Properties and Applications

Cited by 3 publications

References 121 publications

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

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

Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks

Organofluorine chemistry: promising growth areas and challenges

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

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