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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 9, pp 852–858 | Cite as

3-Nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes in reaction with N-methylazomethine ylide: stereoselective synthesis of 3a,4,4-trisubstituted chromeno[3,4-c]pyrrolidines

  • Vladislav Yu. Korotaev
  • Igor B. Kutyashev
  • Alexey Yu. Barkov
  • Vyacheslav Ya. Sosnovskikh
Article
  • 23 Downloads

1,3-Dipolar cycloaddition of unstabilized azomethine ylide obtained in situ from sarcosine and paraform occurred stereoselectively at the double bond of 3-nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes activated by the presence of nitro group. The synthetic procedure required refluxing in benzene for 2 h and gave chromeno[3,4-c]pyrrolidines with trans configuration of trifluoromethyl group and nitro group as the major products. The structure of the obtained products was confirmed by X-ray structural analysis.

Keywords

chromeno[3,4-c]pyrrolidines 3-nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes unstabilized 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

  • Vladislav Yu. Korotaev
    • 1
  • Igor B. Kutyashev
    • 1
  • Alexey Yu. Barkov
    • 1
  • 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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