1440976-13-5Relevant academic research and scientific papers
O-Perhalopyridin-4-yl Hydroxylamines: Amidyl-Radical Generation Scaffolds in Photoinduced Direct Amination of Heterocycles
Zheng, Lan,Qian, Yu-En,Hu, Yuan-Zhuo,Xiao, Jun-An,Ye, Zhi-Peng,Chen, Kai,Xiang, Hao-Yue,Chen, Xiao-Qing,Yang, Hua
, p. 1643 - 1647 (2021)
Reported herein is the design and synthesis of new O-perhalopyridin-4-yl hydroxylamines as shelf-stable and versatile amidyl-radical precursors. The novel amination reagents can be easily prepared via a single synthetic step from inexpensive commercially available starting materials using monoprotected HONH2 as amino source. The synthetic potency of the developed reagents was well demonstrated by direct amination of a series of quinoxalin-2(1H)-ones and their analogues under photocatalytic conditions, even without any additive and photocatalysts.
Amination reagent and synthesis method and application thereof
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, (2021/04/21)
The invention discloses an amination reagent. Corresponding substituent groups can be removed under acidic conditions to obtain quinoxalinone intermediates with 3-site free amino groups, so further functionalization is easy to perform, and many molecules with potential biological activity can be synthesized. Based on the principle, the invention also provides an application of the amination reagent, the amination reagent and N-methylquinoxaline-2-ketone/2H-1, 4-benzoxazine-2-ketone are used as raw materials, the raw materials react under the photocatalytic condition, the N-O bond of the amination reagent is split, and 3-position aza quinoxalinone is synthesized. In the synthesis process, the free radical reaction participating in activation of the CH bond replaces traditional transition metal catalytic activation, and the synthesis process is a simple and environment-friendly mode for synthesizing medicines and modifying natural products. The invention also provides a synthesis method of the amination reagent.
A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles
Brachet, Etienne,Peyrat, Jean-Francois,Brion, Jean-Daniel,Messaoudi, Samir,Alami, Mouad
, p. 3808 - 3816 (2014/03/21)
An efficient and general palladium-catalyzed coupling of 3-chloro-quinoxalinones with a variety of nitrogen-containing nucleophiles such as (hetero)aromatic and aliphatic amides as well as some challenging weakly nucleophilic nitrogen compounds including lactams, carbamates and NH-containing azoles is described. In all cases, the reactions take place rapidly and cleanly in dioxane using Pd(OAc)2 as a catalyst, Xantphos as a ligand and K2CO3 as a base furnishing the coupling 3-N-substituted quinoxalinone products in good to excellent yields. This journal is The Royal Society of Chemistry 2013.
