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Visible Light‐Induced Radical Cyclization of Ethyl 2‐( N ‐Arylcarbamoyl)‐2‐Chloroiminoacetates: Synthesis of Quinoxalin‐2(1 H )‐ones
Author(s) -
Li Dianjun,
Ma Haichao,
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.201500774
Subject(s) - chemistry , radical , photocatalysis , yield (engineering) , photochemistry , solvent , visible spectrum , cleavage (geology) , irradiation , medicinal chemistry , organic chemistry , catalysis , physics , optoelectronics , materials science , geotechnical engineering , fracture (geology) , nuclear physics , engineering , metallurgy
This paper reveals that visible light irradiation with Ru(phen) 3 Cl 2 as photocatalyst can induce ethyl 2‐( N ‐arylcarbamoyl)‐2‐chloroiminoacetates to undergo NCl cleavage to give α‐(aminocarbonyl)iminyl radicals under an argon atmosphere. The subsequent cyclization of the thus formed iminyl radicals affords quinoxalin‐2(1 H )‐one products in good yield in the presence of an inorganic base such as Na 2 CO 3 . The reactions proceeded very well even without using a photocatalyst when DMF was used as the solvent. These protocols provide a new, simple method for the generation of iminyl radicals, and the reactions described herein constitute an efficient method for the synthesis of quinoxalin‐2(1 H )‐one derivatives.