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An Efficient Synthesis of 2-CF3-3-Benzylindoles.

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.

SUBMITTER: Muzalevskiy VM

PROVIDER: S-EPMC8401147 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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An Efficient Synthesis of 2-CF3-3-Benzylindoles.

Muzalevskiy Vasiliy M VM Sizova Zoia A ZA Nenajdenko Valentine G VG

Molecules (Basel, Switzerland) 20210822 16

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. ...[more]

PMID: 34443672

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