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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 729–738 | Cite as

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

  • Maryana А. Nadirova
  • Kuz’ma M. Pokazeev
  • Irina А. Kolesnik
  • Pavel V. Dorovatovskii
  • Nikolay А. BumaginEmail author
  • Vladimir I. Potkin
Article
  • 19 Downloads

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.

Keywords

furan isoindole 7-oxabicyclo[2.2.1]heptene [4+2] cycloaddition esterification IMDAF reaction intramolecular Diels–Alder reaction 

Notes

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).

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Maryana А. Nadirova
    • 1
  • Kuz’ma M. Pokazeev
    • 2
  • Irina А. Kolesnik
    • 2
  • Pavel V. Dorovatovskii
    • 3
  • Nikolay А. Bumagin
    • 4
    Email author
  • Vladimir I. Potkin
    • 2
  1. 1.Institute of Organic and Macromolecular ChemistryHeinrich Heine University DüsseldorfDüsseldorfGermany
  2. 2.Institute of Physical Organic Chemistry, National Academy of Sciences of BelarusMinskBelarus
  3. 3.National Research Center “Kurchatov Institute”MoscowRussia
  4. 4.M. V. Lomonosov Moscow State UniversityMoscowRussia

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