Visible Light‐Induced Radical Cyclization of Ethyl 2‐( N ‐Arylcarbamoyl)‐2‐Chloroiminoacetates: Synthesis of Quinoxalin‐2(1 H )‐ones | Zendy

Li Dianjun | Zendy; Ma Haichao | Zendy; Yu Wei | Zendy

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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.

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