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N ‐Bromosuccinimide‐Mediated Radical Cyclization of 3‐Arylallyl Azides: Synthesis of 3‐Substituted Quinolines
Author(s) -
Wang WeiXia,
Zhang QingZhao,
Zhang TianQi,
Li ZhanShan,
Zhang Wei,
Yu Wei
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400637
Subject(s) - chemistry , n bromosuccinimide , quinoline , radical , intramolecular force , hydrogen atom abstraction , ring (chemistry) , medicinal chemistry , aryl , aryl radical , photochemistry , organic chemistry , halogenation , alkyl
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 abstraction 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.