Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki–Miyaura coupling reactions

The synthesis and characterization of substituted (trifluoromethoxy, thiomethyl, and methoxy) phenyl quinolines is described. Dichlorobis(triphenylphosphine)palladium(II)-catalyzed Suzuki–Miyaura cross-coupling of 6-bromo- and 6,8-dibromo-1,2,3,4-tetrahydroquinolines, 5-bromo-8-methoxyquinoline, and...

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Bibliographic Details
Published in:Journal of chemical research 2019-07, Vol.43 (7-8), p.274-280
Main Author: Ökten, Salih
Format: Article
Language:English
Subjects:
Acids
Aromatic compounds
Breast cancer
Chemical reactions
Chemical synthesis
Cross coupling
Enzymes
Fourier transforms
Infrared analysis
NMR
Nuclear magnetic resonance
Organic compounds
Palladium
Substitutes
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Summary:The synthesis and characterization of substituted (trifluoromethoxy, thiomethyl, and methoxy) phenyl quinolines is described. Dichlorobis(triphenylphosphine)palladium(II)-catalyzed Suzuki–Miyaura cross-coupling of 6-bromo- and 6,8-dibromo-1,2,3,4-tetrahydroquinolines, 5-bromo-8-methoxyquinoline, and 5,7-dibromo-8-methoxyquinoline with substituted phenylboronic acids affords the corresponding 6-aryl- (13a–d), 6,8-diaryl- (14a–c), 5-aryl- (15), and 5,7-diaryl- (16b, c) tetrahydroquinolines and quinolines in high yields (68%–82%). The structures of all the products are characterized by 1H NMR, 13C NMR,19F NMR, and Fourier transform infrared spectroscopy and by elemental analysis.
ISSN:1747-5198
2047-6507
DOI:10.1177/1747519819861389