Issue 19, 2021

Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes

Abstract

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.

Graphical abstract: Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2021
Accepted
07 Apr 2021
First published
09 Apr 2021

Org. Biomol. Chem., 2021,19, 4303-4319

Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes

V. M. Muzalevskiy, Z. A. Sizova, V. T. Abaev and V. G. Nenajdenko, Org. Biomol. Chem., 2021, 19, 4303 DOI: 10.1039/D1OB00098E

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