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[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines

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Chemistry of Heterocyclic Compounds Aims and scope

Cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing an alkoxycarbonyl, sulfonyl, sulfoximine, or sulfamide substituent in position 1 with ethyl isocyanoacetate proceed with the formation of 3-(trifluoromethyl)-2,3-dihydro-1H-pyrroles, whereas their reactions with tosylmethyl isocyanide lead to the formation of 4-(trifluoromethyl)-1H-pyrroles.

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Notes

  1. Hereinafter in the Experimental, the signals of the major isomer are indicated with an asterisk (*), signals of both isomers are indicated with two asterisks (**).

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St, Kyiv, 02660, Ukraine

    Yuriy N. Markitanov, Vadim M. Timoshenko, Eduard B. Rusanov & Yuriy G. Shermolovich

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  1. Yuriy N. Markitanov
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  2. Vadim M. Timoshenko
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  3. Eduard B. Rusanov
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  4. Yuriy G. Shermolovich
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Correspondence to Vadim M. Timoshenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(3), 253–260

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Markitanov, Y.N., Timoshenko, V.M., Rusanov, E.B. et al. [3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines. Chem Heterocycl Comp 57, 253–260 (2021). https://doi.org/10.1007/s10593-021-02901-x

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