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Different behavior of azomethine ylides derived from 11H-indeno[1,2-b]quinoxalin-11-one and proline/sarcosine in reactions with 3-nitro-2H-chromenes

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Chemistry of Heterocyclic Compounds Aims and scope

(3+2) Cycloaddition of azomethine ylide generated in situ from 11H-indeno[1,2-b]quinoxalin-11-one and proline to 3-nitro-2-trifluoro- (trichloro)methyl- and 3-nitro-2-phenyl-2H-chromenes upon heating in EtOH proceeded regio- and stereoselectively, resulting in the formation of spiro[chromeno[3,4-a]pyrrolizine-11,11'-indeno[1,2-b]quinoxalines]. An analogous reaction using ylide derived from sarcosine under the conditions of kinetic control led to preferential formation of diastereomeric spiro[chromeno[3,4-c]pyrrolidine-3,11'-indeno[1,2-b]quinoxalines] with different configuration of the spiro atom, which were transformed upon heating in DMSO into the thermodynamically more stable spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines].

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This work received financial support from the Russian Foundation for Basic Research (grant 18-33-00635) and within the framework of State Assignment of the Ministry of Science and Higher Education of the Russian Federation (project 4.6653.2017/8.9).

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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 Ave., Yekaterinburg, 620000, Russia

    Igor B. Kutyashev, 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. Alexey Yu. Barkov
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  3. Nikolay S. Zimnitskiy
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  4. Vladislav Yu. Korotaev
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  5. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vladislav Yu. Korotaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(9), 861–874

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Kutyashev, I.B., Barkov, A.Y., Zimnitskiy, N.S. et al. Different behavior of azomethine ylides derived from 11H-indeno[1,2-b]quinoxalin-11-one and proline/sarcosine in reactions with 3-nitro-2H-chromenes. Chem Heterocycl Comp 55, 861–874 (2019). https://doi.org/10.1007/s10593-019-02550-1

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