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

Ramani Gurubrahamam; Koppanathi Nagaraju; Kwunmin Chen

doi:10.1039/c8cc02565g

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

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	https://doi.org/10.1039/c8cc02565g
Publication status	Published - 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

Access to Document

10.1039/c8cc02565g

Cite this

@article{06a5cf7d2fc349a8a03f2e8b6c2b8f42,

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

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.",

author = "Ramani Gurubrahamam and Koppanathi Nagaraju and Kwunmin Chen",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc02565g",

language = "English",

volume = "54",

pages = "6048--6051",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "47",

}

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

Y1 - 2018

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 - https://www.scopus.com/pages/publications/85048371773

UR - https://www.scopus.com/pages/publications/85048371773#tab=citedBy

U2 - 10.1039/c8cc02565g

DO - 10.1039/c8cc02565g

M3 - Article

C2 - 29799038

AN - SCOPUS:85048371773

SN - 1359-7345

VL - 54

SP - 6048

EP - 6051

JO - Chemical Communications

JF - Chemical Communications

IS - 47

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this