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Electrophilic Fluorination of Imidazoheterocycles by Selectfluor

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Abstract

Response surface analysis (RSA) has been used for optimization of the synthesis using selectfluor as a fluorine source and 2-ethyl-7-methylimidazole[1,2-a]pyridine-2, 7-dicarboxylate as a substrate. The latter has been synthesized by cyclization of methyl 2-aminopyridine-3-formate with ethyl bromopyruvate. The optimal reaction conditions have been determined to be as follows: time 3 h, temperature 30°C and selectfluor rate 2.3 eq. The triplicated verification experiments have led to the average yield of 87%. Four other fluorides of imidazoheterocycles have been synthesized under the optimized conditions. Structures of fluorides have been supported by 1H NMR.

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Funding

This work was supported by the Science and Technology Cooperation Project in Guizhou Province (LH20177252), the Science and Technology Development Project of Guizhou Technology Program (SY20133092, SY20143052) and the Guizhou University’s Academic New Seedling Cultivation and Innovation Exploration Project in 2017 (20175788).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guizhou University, 550025, Guiyang, China

    Feng Wu, Tong Liu & Wanpeng Liao

  2. Guizhou Engineering Laboratory for Synthetic Drugs, 550025, Guiyang, China

    Feng Wu, Wanpeng Liao, Zhixu Zhou & Hongyu Dai

  3. School of Pharmaceutical Sciences, Guizhou University, 550025, Guiyang, China

    Zhixu Zhou & Hongyu Dai

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  1. Feng Wu
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  2. Tong Liu
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  3. Wanpeng Liao
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Correspondence to Tong Liu.

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Wu, F., Liu, T., Liao, W. et al. Electrophilic Fluorination of Imidazoheterocycles by Selectfluor. Russ J Gen Chem 92, 1333–1339 (2022). https://doi.org/10.1134/S1070363222070234

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