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

Autor:	Wei Yu, Wei-Xia Wang, Tianqi Zhang, Wei Zhang, Qingzhao Zhang, Zhan-Shan Li
Rok vydání:	2014
Předmět:	chemistry.chemical_compound chemistry Aryl Radical Intramolecular force Quinoline Visible light irradiation General Chemistry N-Bromosuccinimide Ring (chemistry) Photochemistry Medicinal chemistry Radical cyclization
Zdroj:	Advanced Synthesis & Catalysis. 357:221-226
ISSN:	1615-4150
DOI:	10.1002/adsc.201400637
Popis:	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 a-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.
Databáze:	OpenAIRE
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