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A simple synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and N-aryltrifluoroacetimidoyl chlorides

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Chemistry of Heterocyclic Compounds Aims and scope

A novel synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and trifluoromethylated imidoyl chlorides in acetonitrile as solvent at room temperature without any catalyst is described. The FT-IR, 1H, 13C, 19F NMR spectral and elemental analysis confirm the structures of products. The synthesized azomethine ylides are easily purified by washing with diethyl ether and are stable even at high temperature. Heating of these ylides in refluxing acetonitrile, ethanol, or DMSO did not result in the intramolecular cyclization to imidazopyridine derivatives and only starting ylides were isolated.

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We gratefully acknowledge the Vail-e-Asr University of Rafsanjan Faculty Research Grant for financial support.

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Authors and Affiliations

  1. Department of chemistry, Vali-e-Asr University, Rafsanjan, 77176, Iran

    Mahdiyeh Talebizadeh, Mohammad Anary-Abbasinejad & Ali Darekordi

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  1. Mahdiyeh Talebizadeh
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  2. Mohammad Anary-Abbasinejad
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  3. Ali Darekordi
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Correspondence to Mohammad Anary-Abbasinejad.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 235–239

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Talebizadeh, M., Anary-Abbasinejad, M. & Darekordi, A. A simple synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and N-aryltrifluoroacetimidoyl chlorides. Chem Heterocycl Comp 55, 235–239 (2019). https://doi.org/10.1007/s10593-019-02447-z

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  • DOI: https://doi.org/10.1007/s10593-019-02447-z

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