Synthesis of Isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepines via N-Acyliminium Cyclization

L. V. Lenshmidt, M. S. Ledovskaya, A. G. Larina, A. S. Filatov, O. B. Chakchir, A. V. Stepakov

Research output: Contribution to journalArticlepeer-review

Abstract

Fused polycyclic compounds with benzo[c]isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepine, dibenzo[c,e]isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepine, and benzo[f]isoxazolo[5',4':3,4]pyrrolo[1,2-d]oxazepine cores are readily available via cyclization of the N-acyliminium cation generated from the corresponding 6-hydoxy-5-R-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazol-4(5H)-ones in the presence of BF3·Et2O or Sn(NTf2)4.
Original languageEnglish
Pages (from-to)234-245
JournalRussian Journal of Organic Chemistry
Volume56
Issue number2
DOIs
StatePublished - Apr 2020

Keywords

  • N-acyliminium cyclization
  • pyrrolo[2,1-a]azepines
  • hydroxylactams
  • isoxazolines
  • Lewis acid
  • stereselective reaction
  • chemoselective reduction
  • 1,3-dipolar cycloaddition

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