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Unexpected regiochemistry in [3+2] cycloaddition reaction of azomethine ylides of indenoquinoxalinone series to arylidene malononitriles

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Chemistry of Heterocyclic Compounds Aims and scope

1,3-Dipolar cycloaddition of azomethine ylides generated in situ from proline and indenoquinoxalinones occurred at the double bond of arylidene malononitriles upon heating in isopropanol, leading to the respective spirocyclic adducts with cis orientation of the aryl substituent and the quinoxaline moiety. The regioselectivity of this process depended on the electron donor-acceptor properties of substituents in the aromatic ring of the dipolarophile molecule. Analogous reaction involving azomethine ylide derived from sarcosine produced adducts with a trans relationship of the most sterically demanding substituents.

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This work received financial support from the Ministry of Education and Science of the Russian Federation (agreement 02.A03.21.0006).

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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

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

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  1. Alexey Yu. Barkov
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  2. Nikolay S. Zimnitskiy
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  3. Igor B. Kutyashev
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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, 2018, 54(1), 43–50

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Barkov, A.Y., Zimnitskiy, N.S., Kutyashev, I.B. et al. Unexpected regiochemistry in [3+2] cycloaddition reaction of azomethine ylides of indenoquinoxalinone series to arylidene malononitriles. Chem Heterocycl Comp 54, 43–50 (2018). https://doi.org/10.1007/s10593-018-2228-8

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  • DOI: https://doi.org/10.1007/s10593-018-2228-8

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