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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1315–1323 | Cite as

Regio- and stereoselective 1,3-dipolar cycloaddition reactions between arylideneacetones and stabilized azomethine ylides obtained from ninhydrin and indenoquinoxalinones

  • Alexey Yu. Barkov
  • Nikolay S. Zimnitskiy
  • Igor B. Kutyashev
  • Vladislav Yu. KorotaevEmail author
  • Vyacheslav Ya. Sosnovskikh
Article

Stabilized azomethine ylides, generated in situ from proline/sarcosine and ninhydrin or indenoquinoxalinones, underwent 1,3-dipolar cycloaddition at the activated double bond of arylideneacetones, leading predominantly to endo-spiro adducts. These products formed as a result of addition between the less substituted carbon atom of azomethine ylide and the most electrophilic site of the dipolarophile.

Keywords

arylideneacetones spiropyrrolidines spiropyrrolizidines stabilized azomethine ylides 1,3-dipolar cycloaddition 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Alexey Yu. Barkov
    • 1
  • Nikolay S. Zimnitskiy
    • 1
  • Igor B. Kutyashev
    • 1
  • Vladislav Yu. Korotaev
    • 1
    Email author
  • Vyacheslav Ya. Sosnovskikh
    • 1
  1. 1.Institute of Natural Sciences and MathematicsUral Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia

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