N-Bromosuccinimide-Mediated Radical Cyclization of 3-Arylallyl Azides: Synthesis of 3-Substituted Quinolines

N-Bromosuccinimide-Mediated Radical Cyclization of 3-Arylallyl Azides: Synthesis of 3-Substituted Quinolines

Visible light irradiation of N‐bromosuccinimide serves as an effective means to convert methyl 2‐(azidomethyl)‐3‐arylpropenoates and 2‐(azidomethyl)‐3‐arylacrylonitriles to the corresponding iminyl radicals via α‐hydrogen ion and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then u...

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Veröffentlicht in:Advanced synthesis & catalysis 2015-01, Vol.357 (1), p.221-226
Hauptverfasser: Wang, Wei-Xia, Zhang, Qing-Zhao, Zhang, Tian-Qi, Li, Zhan-Shan, Zhang, Wei, Yu, Wei
Format: Artikel
Sprache:eng
Schlagworte:
2-(azidomethyl)-3-arylacrylonitriles
2-(azidomethyl)-3-arylpropenoates
3-substituted quinolines
Aromatic compounds
Catalysis
cyclization
Extrusion
iminyl radicals
Light irradiation
N-bromosuccinimide
Quinoline
Radicals
Synthesis
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Zusammenfassung:Visible light irradiation of N‐bromosuccinimide serves as an effective means to convert methyl 2‐(azidomethyl)‐3‐arylpropenoates and 2‐(azidomethyl)‐3‐arylacrylonitriles to the corresponding iminyl radicals via α‐hydrogen ion and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quinoline‐3‐carboxylates and quinoline‐3‐carbonitriles respectively.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400637