An Efficient Synthesis of 2-CF3-3-Benzylindoles

Vasiliy M Muzalevskiy; Zoia A Sizova; Valentine G Nenajdenko

doi:10.3390/molecules26165084

An Efficient Synthesis of 2-CF₃-3-Benzylindoles

Molecules. 2021 Aug 22;26(16):5084. doi: 10.3390/molecules26165084.

Authors

Vasiliy M Muzalevskiy¹, Zoia A Sizova¹, Valentine G Nenajdenko¹

Affiliation

¹ Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, Russia.

Abstract

The reaction of α-CF₃-β-(2-nitroaryl) enamines with benzaldehydes afforded effectively α,β-diaryl-CF₃-enones having nitro group. Subsequent reduction of nitro group by NH₄HCO₂-Pd/C system initiated intramolecular cyclization to give 2-CF₃-3-benzylindoles. Target products can be prepared in up to quantitative yields. Broad synthetic scope of the reaction was shown. Probable mechanism of indole formation is proposed.

Keywords: CF3-group; ammonium formate; enone; fluorine; indole; nitro; reduction.

Grants and funding

18-13-00136/Russian Science Foundation