Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes

α-CF3-enamines can be prepared by the reaction of pyrrolidine with the corresponding haloalkenes. The prepared enamines react with 2-nitrobenzaldehydes to give ortho-nitro-substituted α,β-diaryl-CF3-enones highly stereoselectively in up to 88% yield. Subsequent reduction of the nitro-group by an Fe–...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-05, Vol.19 (19), p.4303-4319
Main Authors: Muzalevskiy, Vasiliy M, Sizova, Zoia A, Abaev, Vladimir T, Nenajdenko, Valentine G
Format: Article
Language:English
Subjects:
Alkenes
NMR
Nuclear magnetic resonance
Organic compounds
Pyrrolidine
Quinolines
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Summary:α-CF3-enamines can be prepared by the reaction of pyrrolidine with the corresponding haloalkenes. The prepared enamines react with 2-nitrobenzaldehydes to give ortho-nitro-substituted α,β-diaryl-CF3-enones highly stereoselectively in up to 88% yield. Subsequent reduction of the nitro-group by an Fe–AcOH system promotes intramolecular cyclization to afford 2-CF3-3-arylquinolines in up to 99% isolated yield. High synthetic utility of all synthetic steps of the sequence was shown. A one-pot procedure was developed to give the target trifluoromethylated quinolines directly from enamines or haloalkenes.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00098e