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Regio- and Stereoselective 1,3-dipolar Cycloaddition of Azomethine Ylides Based on Isatins and (thia)proline to 3-nitro-2-(trifluoro(trichloro)methyl)-2H-chromenes: Synthesis and Cytotoxic Activity of 6-(trihalomethyl)-spiro[chromeno(thia)pyrrolizidine-11,3'-indolin]-2'-ones

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Chemistry of Heterocyclic Compounds Aims and scope

A regio- and stereoselective method for the synthesis of (trifluoro(trichloro)methyl)-substituted spiro[chromeno(thia)pyrrolizidineoxindoles] in 53–97% yields was developed on the basis of the three-component reaction of 3-nitro-2-(trifluoro(trichloro)methyl)-2Hchromenes with azomethine ylides generated in situ from isatins and L-(thia)proline in EtOH at 30°C. The obtained compounds demonstrated high cytotoxic activity against HeLa human cervical cancer and RD human embryonic rhabdomyosarcoma cells.

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave, Yekaterinburg, 620000, Russia

    Igor B. Kutyashev, Maria V. Ulitko, Alexey Yu. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev & Vyacheslav Ya. Sosnovskikh

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  1. Igor B. Kutyashev
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  2. Maria V. Ulitko
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  3. Alexey Yu. Barkov
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  4. Nikolay S. Zimnitskiy
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  5. Vladislav Yu. Korotaev
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  6. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vladislav Yu. Korotaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 751–763

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Kutyashev, I.B., Ulitko, M.V., Barkov, A.Y. et al. Regio- and Stereoselective 1,3-dipolar Cycloaddition of Azomethine Ylides Based on Isatins and (thia)proline to 3-nitro-2-(trifluoro(trichloro)methyl)-2H-chromenes: Synthesis and Cytotoxic Activity of 6-(trihalomethyl)-spiro[chromeno(thia)pyrrolizidine-11,3'-indolin]-2'-ones. Chem Heterocycl Comp 57, 751–763 (2021). https://doi.org/10.1007/s10593-021-02979-3

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