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Synthesis and Structure of Esterification Products of 6-aryl-1,2,3,6,7,7a-hexahydro-3а,6-epoxyisoindole-7-carboxylic Acids

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Chemistry of Heterocyclic Compounds Aims and scope

It was found that the reaction of 5-arylfurfurilamines with maleic anhydride leads to the formation of 6-aryl-3a,6-epoxyisoindole-7-carboxylic acids (the cyclic form), which in solution are in dynamic equilibrium with N-furfurylmaleinamides (the open form). During the esterification of these tautomeric mixtures with methanol in the presence of a catalytic amount of sulfuric acid, methyl esters of 5-aryl-7a-hydroxy-7-methoxy-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindole-4-carboxylic acids, unexpected cleavage products of the 3a,6-oxo bridge of the cyclic form, are formed diastereospecifically. The structure of the obtained products was confirmed by X-ray structural analysis.

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This work was financially supported by the Russian Foundation for Basic Research (grants 18-58-00013-Bel_a, 19-53-04002) and the Belarusian Republican Foundation for Fundamental Research (grants Х18Р-010, Х19РМ-003).

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Authors and Affiliations

  1. Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, 1 Universitäts St., 40225, Düsseldorf, Germany

    Maryana А. Nadirova

  2. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., 220072, Minsk, Belarus

    Kuz’ma M. Pokazeev, Irina А. Kolesnik & Vladimir I. Potkin

  3. National Research Center “Kurchatov Institute”, 1 Akademika Kurchatova Sq., Moscow, 123182, Russia

    Pavel V. Dorovatovskii

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

    Nikolay А. Bumagin

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  1. Maryana А. Nadirova
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  2. Kuz’ma M. Pokazeev
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  3. Irina А. Kolesnik
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  4. Pavel V. Dorovatovskii
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  5. Nikolay А. Bumagin
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  6. Vladimir I. Potkin
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Correspondence to Nikolay А. Bumagin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 729–738

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Nadirova, M.А., Pokazeev, K.M., Kolesnik, I.А. et al. Synthesis and Structure of Esterification Products of 6-aryl-1,2,3,6,7,7a-hexahydro-3а,6-epoxyisoindole-7-carboxylic Acids. Chem Heterocycl Comp 55, 729–738 (2019). https://doi.org/10.1007/s10593-019-02528-z

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