Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization

Expeditious access to oxadiazepines via 1,5-hydride shift/cyclization of pyrrolidine- or tetrahydroisoquinoline-containing nitrones has been developed. With 1,3-dipole nitrones serving as the hydride acceptors, this transformation was promoted by a Lewis acid, providing access to structurally divers...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 19; pp. 9620 - 9627
Main Authors Chang, Yong-Zhi, Li, Ming-Lei, Zhao, Wen-Feng, Wen, Xiaoan, Sun, Hongbin, Xu, Qing-Long
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GOLD
ACTIVATION
AMINATION
ASYMMETRIC-SYNTHESIS
TETRAHYDROQUINOLINES
ALKYNYL ETHERS
INTRAMOLECULAR REDOX REACTION
H BOND FUNCTIONALIZATION
CYCLIZATION
CYCLIC AMINALS
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Summary:Expeditious access to oxadiazepines via 1,5-hydride shift/cyclization of pyrrolidine- or tetrahydroisoquinoline-containing nitrones has been developed. With 1,3-dipole nitrones serving as the hydride acceptors, this transformation was promoted by a Lewis acid, providing access to structurally diverse oxadiazepines in good yields. A one-pot process for in situ nitrone formation, a 1,5-hydride shift, and ring cyclization was also realized.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01609