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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 9, pp 861–874 | Cite as

Different behavior of azomethine ylides derived from 11H-indeno[1,2-b]quinoxalin-11-one and proline/sarcosine in reactions with 3-nitro-2H-chromenes

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

(3+2) Cycloaddition of azomethine ylide generated in situ from 11H-indeno[1,2-b]quinoxalin-11-one and proline to 3-nitro-2-trifluoro- (trichloro)methyl- and 3-nitro-2-phenyl-2H-chromenes upon heating in EtOH proceeded regio- and stereoselectively, resulting in the formation of spiro[chromeno[3,4-a]pyrrolizine-11,11'-indeno[1,2-b]quinoxalines]. An analogous reaction using ylide derived from sarcosine under the conditions of kinetic control led to preferential formation of diastereomeric spiro[chromeno[3,4-c]pyrrolidine-3,11'-indeno[1,2-b]quinoxalines] with different configuration of the spiro atom, which were transformed upon heating in DMSO into the thermodynamically more stable spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines].

Keywords

azomethine ylides 11H-indeno[1,2-b]quinoxalin-11-one 3-nitro-2H-chromenes proline sarcosine spirochromeno[3,4-c]- pyrrolidines spirochromeno[3,4-a]pyrrolizidines (3+2) cycloaddition 

Notes

This work received financial support from the Russian Foundation for Basic Research (grant 18-33-00635) and within the framework of State Assignment of the Ministry of Science and Higher Education of the Russian Federation (project 4.6653.2017/8.9).

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Copyright information

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

Authors and Affiliations

  • Igor B. Kutyashev
    • 1
  • Alexey Yu. Barkov
    • 1
  • Nikolay S. Zimnitskiy
    • 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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