76052-78-3Relevant academic research and scientific papers
Synthesis of (E)-Quinoxalinone Oximes through a Multicomponent Reaction under Mild Conditions
Xu, Jun,Yang, Huiyong,He, Lei,Huang, Lin,Shen, Jiabin,Li, Wanmei,Zhang, Pengfei
supporting information, p. 195 - 201 (2021/01/13)
Herein, a novel method for the gram-scale synthesis of (E)-quinoxalinone oximes through a multicomponent reaction under mild conditions is described. Such a transformation was performed under transition-metal-free conditions, affording (E)-oximes in a moderate-to-good yield through recrystallization. Our methodology demonstrates a successful combination of a Mannich-type reaction and radical coupling, providing a green and practical approach for the synthesis of potentially bioactive quinoxalinone-containing molecules.
Rapid alkenylation of quinoxalin-2(1H)-ones enabled by the sequential Mannich-type reaction and solar photocatalysis
Huang, Lin,Xu, Jun,He, Lei,Liang, Chenfeng,Ouyang, Yani,Yu, Yongping,Li, Wanmei,Zhang, Pengfei
supporting information, p. 3627 - 3631 (2021/05/03)
Herein, a rapid alkenylation of quinoxalin-2(1H)-ones enabled by a combination of Mannich-type reaction and solar photocatalysis is demonstrated. A wide range of functional groups are compatible, affording the corresponding products in moderate-to-good yields. Control experiments illustrate that the in situ generated 1O2 plays a central role in this reaction. This green and efficient strategy provides a practical solution for the synthesis of potentially bioactive compounds that containing a 3,4-dihydroquinoxalin-2(1H)-one structure.
N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes
Liu, Fang,Ye, Zhi-Peng,Hu, Yuan-Zhuo,Gao, Jie,Zheng, Lan,Chen, Kai,Xiang, Hao-Yue,Chen, Xiao-Qing,Yang, Hua
, p. 11905 - 11914 (2021/08/24)
Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.
Nickel-catalyzed electrochemical reductive decarboxylative coupling of: N -hydroxyphthalimide esters with quinoxalinones
Lian, Fei,Xu, Kun,Meng, Wei,Zhang, Haonan,Tan, Zhoumei,Zeng, Chengchu
supporting information, p. 14685 - 14688 (2019/12/11)
Herein the first example of electrochemically enabled, NiCl2-catalyzed reductive decarboxylative coupling of N-hydroxyphthalimide (NHP) esters with quinoxalinones is reported. A range of primary, secondary, tertiary aliphatic carboxylic acids and amino acid-derived esters were tolerated well. This decarboxylative coupling allows access to structurally diverse 3-alkylated quinoxalinones in up to 91% yields.
Antibacterial activity of quinoxalines, quinazolines, and 1,5-naphthyridines
Parhi, Ajit K.,Zhang, Yongzheng,Saionz, Kurt W.,Pradhan, Padmanava,Kaul, Malvika,Trivedi, Kalkal,Pilch, Daniel S.,Lavoie, Edmond J.
, p. 4968 - 4974 (2013/09/02)
Several phenyl substituted naphthalenes and isoquinolines have been identified as antibacterial agents that inhibit FtsZ-Zing formation. In the present study we evaluated the antibacterial of several phenyl substituted quinoxalines, quinazolines and 1,5-naphthyridines against methicillin-sensitive and methicillin-resistant Staphylococcus aureus and vancomycin-sensitive and vancomycin-resistant Enterococcus faecalis. Some of the more active compounds against S. aureus were evaluated for their effect on FtsZ protein polymerization. Further studies were also performed to assess their relative bactericidal and bacteriostatic activities. The notable differences observed between nonquaternized and quaternized quinoxaline derivatives suggest that differing mechanisms of action are associated with their antibacterial properties.
