|
KMID : 0043320210440111012
|
|
Archives of Pharmacal Research
2021 Volume.44 No. 11 p.1012 ~ p.1023
|
|
|
Site-selective and metal-free C?H nitration of biologically relevant N-heterocycles
|
|
Moon Junghyea
Ji Hyun-Ku
Ko Na-Young
Oh Ha-Rin
Park Min-Seo
Kim Su-Ho
Ghosh Prithwish
Mishra Neeraj Kumar
Kim In-Su
|
|
|
Abstract
|
|
|
|
The site-selective and metal-free C?H nitration reaction of quinoxalinones and pyrazinones as biologically important N-heterocycles with t-butyl nitrite is described. A wide range of quinoxalinones were efficiently applied in this transformation, providing C7-nitrated quinoxalinones without undergoing C3-nitration. From the view of mechanistic point, the radical addition reaction exclusively occurred at the electron-rich aromatic region beyond electron-deficient N-heterocycle ring. This is a first report on the C7?H functionalization of quinoxalinones under metal-free conditions. In contrast, the nitration reaction readily takes place at the C3-position of pyrazinones. This transformation is characterized by the scale-up compatibility, mild reaction conditions, and excellent functional group tolerance. The applicability of the developed method is showcased by the selective reduction of NO2 functionality on the C7-nitrated quinoxalinone product, providing aniline derivatives. Combined mechanistic investigations aided the elucidation of a plausible reaction mechanism.
|
|
|
KEYWORD
|
|
|
t-Butyl nitrite, C?H functionalization, Regioselectivity, Heterocycles, Nitration
|
|
|
FullTexts / Linksout information
|
|
|
|
|
|
Listed journal information
|
|
  
|