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3-Nitro-2-phenyl-2-trifluoromethyl-2H-chromenes in reactions with azomethine ylides from isatins and (thia)proline: synthesis of spiro[chromeno(thia)pyrrolizidine-11,3'-oxindoles]

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Chemistry of Heterocyclic Compounds Aims and scope

1,3-Dipolar cycloaddition of stabilized azomethine ylides generated in situ from isatins and proline to 3-nitro-2-phenyl-2-trifluoromethyl-2H-chromenes in i-PrOH proceeds stereoselectively at room temperature and leads to the formation of hexahydro-6H-spiro[chromeno[3,4-a]-pyrrolizine-11,3'-indolin]-2'-ones with the cis arrangement of the trifluoromethyl group and the nitro group. A similar reaction with the participation of thiaproline-based ylides at 50°С leads to mixtures of diastereomeric tetrahydro-6H,9H-spiro[chromeno[3',4':3,4]pyrrolo[1,2-c]thiazole-11,3'-indolin]-2'-ones with a predominance of the cis- or trans-isomer. The stereochemistry of the obtained products was confirmed by the NOESY experiment and X-ray structural analysis.

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This work was carried out with the financial support of the Russian Foundation for Basic Research (project 20-03-00716) and within the framework of the State Assignment of the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2020-0052).

The authors are grateful to the staff of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds” of Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences and the Laboratory for Complex Research and Expert Evaluation of Organic Materials of Ural Federal University for assistance in carrying out physicochemical analyses.

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  1. Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave, Yekaterinburg, 620000, Russia

    Igor B. Kutyashev, Ivan А. Kochnev, Anastasiya А. Cherepkova, Nikolay S. Zimnitskiy, Alexey Yu. Barkov, Vladislav Yu. Korotaev & Vyacheslav Ya. Sosnovskikh

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  1. Igor B. Kutyashev
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  2. Ivan А. Kochnev
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  3. Anastasiya А. Cherepkova
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  4. Nikolay S. Zimnitskiy
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  6. Vladislav Yu. Korotaev
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  7. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vladislav Yu. Korotaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1302–1313

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Kutyashev, I.B., Kochnev, I.А., Cherepkova, A.А. et al. 3-Nitro-2-phenyl-2-trifluoromethyl-2H-chromenes in reactions with azomethine ylides from isatins and (thia)proline: synthesis of spiro[chromeno(thia)pyrrolizidine-11,3'-oxindoles]. Chem Heterocycl Comp 56, 1302–1313 (2020). https://doi.org/10.1007/s10593-020-02815-0

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