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A simple method for the synthesis of isoindoline derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of isoindoline derivatives was developed based on a domino reaction involving a donor-acceptor cyclopropane containing a bromomethyl group in the ortho position of the aromatic substituent and structurally varied primary amines (anilines, benzylamines, cycloalkylamines). It was shown that the resulting N-benzyl-1,3-dihydroisoindole under hydrogenolysis conditions at room temperature underwent selective cleavage of the exocyclic N–CH2Ar bond followed by in situ lactamization to form benzo[b]pyrrolizidinone. The same product was obtained in a domino reaction starting with reduction of the azidomethyl group at the ortho position of the donor aromatic substituent. Similarly, the generation of the o-2-aminoethyl group was accompanied by two successive cyclization reactions leading to the formation of benzo[e]indolizidinone.

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Authors and Affiliations

  1. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Vitaly V. Shorokhov, Danila S. Lebedev, Maksim A. Boichenko, Sergey S. Zhokhov & Olga A. Ivanova

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Igor V. Trushkov

Authors
  1. Vitaly V. Shorokhov
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  2. Danila S. Lebedev
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  3. Maksim A. Boichenko
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  4. Sergey S. Zhokhov
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  5. Igor V. Trushkov
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  6. Olga A. Ivanova
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Correspondence to Olga A. Ivanova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(1/2), 54–62

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Shorokhov, V.V., Lebedev, D.S., Boichenko, M.A. et al. A simple method for the synthesis of isoindoline derivatives. Chem Heterocycl Comp 59, 54–62 (2023). https://doi.org/10.1007/s10593-023-03162-6

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