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Iodine/potassium iodide catalyst for the synthesis of trifluoromethylated quinazolines via intramolecular cyclization of 2,2,2-trifluoro-N-benzyl-N′-arylacetimidamides

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Abstract

An efficient and simple protocol for the synthesis of trifluoromethylated quinazolines has been described by I2-/KI-promoted oxidative C(sp3)–C(sp2) bond under the optimal oxidative cyclization reaction conditions. The required 2,2,2-trifluoro-N-benzyl-N′-arylacetimidamides are readily prepared from the corresponding acetimidoyl chlorides and benzylamines under a nucleophilic substitution reaction in the form of in situ. The merits of this protocol are the use of inexpensive molecular iodine, metal-free oxidative coupling and good to excellent yields.

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Acknowledgements

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

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

    Ali Darehkordi & Elham Kazemi

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  1. Ali Darehkordi
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  2. Elham Kazemi
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Correspondence to Ali Darehkordi.

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Darehkordi, A., Kazemi, E. Iodine/potassium iodide catalyst for the synthesis of trifluoromethylated quinazolines via intramolecular cyclization of 2,2,2-trifluoro-N-benzyl-N′-arylacetimidamides. Mol Divers 24, 131–139 (2020). https://doi.org/10.1007/s11030-019-09933-8

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