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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 4, pp 451–457 | Cite as

Intramolecular [4+2] cycloaddition in N-allyl- and N-propargyl-α-furyl lactams

  • Dmitry S. Poplevin
  • Eugeniya V. Nikitina
  • Vladimir P. Zaytsev
  • Alexey V. Varlamov
  • Santosh G. Tilve
  • Fedor I. Zubkov
Article

The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.

Keywords

epoxyisoindoles furans lactams IMDAF reaction intramolecular [4+2] cycloaddition 

Notes

Synthesis of the starting compounds 2 and 3 was supported by the Russian Foundation for Basic Research (grant No. 17-53-45016). The synthesis and NMR spectroscopy of adducts 4 were performed with financial support from the RUDN University program ''5-100''.

Supplementary material

10593_2018_2290_MOESM1_ESM.pdf (6.1 mb)
ESM 1 (PDF 6197 kb)

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Copyright information

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

Authors and Affiliations

  • Dmitry S. Poplevin
    • 1
  • Eugeniya V. Nikitina
    • 1
  • Vladimir P. Zaytsev
    • 1
  • Alexey V. Varlamov
    • 1
  • Santosh G. Tilve
    • 2
  • Fedor I. Zubkov
    • 1
  1. 1.RUDN UniversityMoscowRussia
  2. 2.Goa UniversityTaleigao PlateauIndia

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