Tricyclic 2-benzazepines obtained via an unexpected cyclization involving nitrilium ylides

Attempted use of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in the Rh(ii)-catalyzed condensation with nitriles to form 1,3-oxazoles led to an unexpected outcome. The nitrilium ylide species thought to form on Rh(ii)-catalyzed decomposition of diazo compounds underwent a cyclization onto the nearb...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 23; pp. 5068 - 5071
Main Authors Inyutina, Anna, Dar'in, Dmitry, Kantin, Grigory, Krasavin, Mikhail
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 16.06.2021
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Crystallography
Cyanide
Diketones
Nitriles
NMR
Nuclear magnetic resonance
Oxazoles
Physical Sciences
Science & Technology
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Summary:Attempted use of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in the Rh(ii)-catalyzed condensation with nitriles to form 1,3-oxazoles led to an unexpected outcome. The nitrilium ylide species thought to form on Rh(ii)-catalyzed decomposition of diazo compounds underwent a cyclization onto the nearby arylidene moiety followed by 1,5-hydride shift. This led to the formation of a 2-benzazepine core which has special significance for drug discovery and can be considered a privileged scaffold.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00773d