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I2/KI-Catalyzed synthesis of 5-trifluoromethylated 1,2,4,6-tetrazepine-3-thiones by annulation of trifluoroacetimidoyl chlorides and thiosemicarbazones

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Abstract

An efficient and simple protocol for the synthesis of trifluoromethylated 1,2,4,6-tetrazepines by intramolecular cross-coupling of C(sp2)–H and N–H bonds using I2/KI catalyst under aerobic oxidative has been demonstrated. This research exhibited a nucleophilic substitution reaction and then oxidative cyclization between trifluoroacetimidoyl chlorides and thiosemicarbazones.

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Acknowledgments

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

    Ali Darehkordi, Farzaneh Nejad Khorasani, Marziyeh Mohammadi & Elham Kazemi

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  1. Ali Darehkordi
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  2. Farzaneh Nejad Khorasani
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  3. Marziyeh Mohammadi
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  4. Elham Kazemi
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Correspondence to Ali Darehkordi.

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Darehkordi, A., Khorasani, F.N., Mohammadi, M. et al. I2/KI-Catalyzed synthesis of 5-trifluoromethylated 1,2,4,6-tetrazepine-3-thiones by annulation of trifluoroacetimidoyl chlorides and thiosemicarbazones. Monatsh Chem 151, 1835–1839 (2020). https://doi.org/10.1007/s00706-020-02703-5

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  • DOI: https://doi.org/10.1007/s00706-020-02703-5

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