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Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines

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Chemistry of Heterocyclic Compounds Aims and scope

A new variant of Hantzsch reaction was developed for the synthesis of 1,2,3,4,5,6,7,8-octahydroquinolines on the basis of regioselective cascade recyclization of N-arylitaconimides in reactions with 3-aminocyclohex-2-enones. The mechanism of this domino process included С-nucleophilic addition of enaminone to the activated multiple bond of itaconimide and intramolecular transamidation with simultaneous recyclization of the intermediate.

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This work was performed with financial support from the Russian Science Foundation (contract No. 18-74-10097).

The results of this study were obtained in part by using the scientific equipment at the Collective Use Center of Voronezh State University.

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya Sq., Voronezh, 394018, Russia

    Yurii A. Kovygin, Khidmet S. Shikhaliev, Mikhail Yu. Krysin, Andrei Yu. Potapov, Irina V. Ledenyova, Yevgeniya A. Kosheleva & Dmitriy Yu. Vandyshev

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  1. Yurii A. Kovygin
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  2. Khidmet S. Shikhaliev
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  3. Mikhail Yu. Krysin
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  4. Andrei Yu. Potapov
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  5. Irina V. Ledenyova
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  6. Yevgeniya A. Kosheleva
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  7. Dmitriy Yu. Vandyshev
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Correspondence to Mikhail Yu. Krysin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 748–754

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Kovygin, Y.A., Shikhaliev, K.S., Krysin, M.Y. et al. Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines. Chem Heterocycl Comp 55, 748–754 (2019). https://doi.org/10.1007/s10593-019-02530-5

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