Abstract
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 language | English |
|---|---|
| Pages (from-to) | 6048-6051 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 54 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - 2018 Jan 1 |
ASJC Scopus subject areas
- Catalysis
- Electronic, Optical and Magnetic Materials
- Ceramics and Composites
- Chemistry(all)
- Surfaces, Coatings and Films
- Metals and Alloys
- Materials Chemistry
Fingerprint Dive into the research topics of 'Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[: B] [1,5]oxazocine heterocycles'. Together they form a unique fingerprint.
Cite this
Gurubrahamam, R., Nagaraju, K., & Chen, K. (2018). Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[: B] [1,5]oxazocine heterocycles. Chemical Communications, 54(47), 6048-6051. https://doi.org/10.1039/c8cc02565g