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 |
Fingerprint
ASJC Scopus subject areas
- Catalysis
- Electronic, Optical and Magnetic Materials
- Ceramics and Composites
- Chemistry(all)
- Surfaces, Coatings and Films
- Metals and Alloys
- Materials Chemistry
Cite this
Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[ : B] [1,5]oxazocine heterocycles. / Gurubrahamam, Ramani; Nagaraju, Koppanathi; Chen, Kwunmin.
In: Chemical Communications, Vol. 54, No. 47, 01.01.2018, p. 6048-6051.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[
T2 - B] [1,5]oxazocine heterocycles
AU - Gurubrahamam, Ramani
AU - Nagaraju, Koppanathi
AU - Chen, Kwunmin
PY - 2018/1/1
Y1 - 2018/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85048371773&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85048371773&partnerID=8YFLogxK
U2 - 10.1039/c8cc02565g
DO - 10.1039/c8cc02565g
M3 - Article
AN - SCOPUS:85048371773
VL - 54
SP - 6048
EP - 6051
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 47
ER -