Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[: B] [1,5]oxazocine heterocycles

Ramani Gurubrahamam, Koppanathi Nagaraju, Kwunmin Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


Metal-free addition of salicylhydrazones to electron deficient internal alkynes catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield oxa-bridged 2,6-epoxybenzo[b][1,5]oxazocine heterocycles was achieved. The demonstrated protocol proceeds through an o-quinone methide formation, aza-Michael addition, stereoselective protonation, enamine promoted aromatization, O,O-acetalization and O,N-aminalization sequence to provide privileged heterocycles in good yields with high diastereoselectivities.

Original languageEnglish
Pages (from-to)6048-6051
Number of pages4
JournalChemical Communications
Issue number47
Publication statusPublished - 2018

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • General Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry


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