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2-Substituted 3-nitro-2H-chromenes in reaction with azomethine ylide derived from ninhydrin and proline: regio- and stereoselective synthesis of spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones

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Chemistry of Heterocyclic Compounds Aims and scope

Regio- and stereoselective 1,3-dipolar cycloaddition of stabilized azomethine ylides, generated in situ from ninhydrin and proline, occurred at the double bond activated by nitro group in 3-nitro-2-(trifluoromethyl)- and 3-nitro-2-phenyl-2H-chromenes upon heating in ethanol. This reaction produced high yields of spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones. The structure of the obtained products was confirmed by the method of X-ray crystallography.

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The work was performed with financial support from the Russian Science Foundation (project 17-73-20070).

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Authors and Affiliations

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

    Vladislav Yu. Korotaev, Igor B. Kutyashev, Alexey Yu. Barkov & Vyacheslav Ya. Sosnovskikh

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  1. Vladislav Yu. Korotaev
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  2. Igor B. Kutyashev
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  3. Alexey Yu. Barkov
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  4. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vladislav Yu. Korotaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(11), 1192–1198

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Korotaev, V.Y., Kutyashev, I.B., Barkov, A.Y. et al. 2-Substituted 3-nitro-2H-chromenes in reaction with azomethine ylide derived from ninhydrin and proline: regio- and stereoselective synthesis of spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones. Chem Heterocycl Comp 53, 1192–1198 (2017). https://doi.org/10.1007/s10593-018-2193-2

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