123464-56-2Relevant academic research and scientific papers
Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation
Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek
, p. 6705 - 6716 (2021/12/31)
We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.
A quantum-chemical approach to develop tetrahydroquinoxaline as potent ferroptosis inhibitors
Lei, Hong-Xu,Zhang, KaiLi,Qin, Yu-Xi,Dong, Rong-Jian,Chen, De-Zhan,Zhou, HaiFeng,Sheng, Xie-Huang
, (2020/11/10)
Ferroptosis is a recently characterized form of regulated necrosis with the iron-dependent accumulation of (phospho)lipid hydroperoxides (LOOH). It has attracted considerable attention for its putative involvement in diverse pathophysiological processes, such as cardiovascular disease and neurodegeneration. Here we describe the discovery of tetrahydroquinoxaline, a novel scaffold of ferroptosis inhibitors based on quantum chemistry methods. Tetrahydroquinoxaline deviates showed very good inhibition of ferroptosis, while being non cytotoxic for human cancer cells. And, the advantage of them is their small molecular weight (MW. = 148 Da) that can be coupled with other drugs to form multi-target drugs to better meet the treatment of complicated diseases.
Bonded- A nd discreted-Lindqvist hexatungstate-based copper hybrids as heterogeneous catalysts for the one-pot synthesis of 2-phenylquinoxalines: Via 2-haloanilines with vinyl azides or 3-phenyl-2 H-azirines
Gong, Shuwen,Huang, Xianqiang,Lv, Xin,Shen, Guodong,Sun, Manman,Tang, Zhenfei,Wang, Zeyou,Zhang, Jiangong
, p. 13993 - 13998 (2020/11/02)
One bonded- A nd one discreted-Lindqvist hexatungstate-based copper hybrids (Cu-POMs) ([Cu2(O)OH (phen)2]2[W6O19]?6H2O (1) and [Cu2(phen)4Cl] [HW6O19]?2H2O (2) (phen = 1,10-phenanthroline)) were controllably synthesized and routinely characterized. Cu-POM
Selective synthesis of (1: H-benzo [d] imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine
Zhan, Zhenzhen,Ma, Haojie,Cui, Xinfeng,Jiang, Pengbo,Pu, Jinghong,Zhang, Yixin,Huang, Guosheng
supporting information, p. 5148 - 5152 (2019/06/03)
We have designed a general, inexpensive, and versatile method for the synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and the formation of C-N bonds via an aromatic aldehyde and o-phenylenediamine. In the presence of N,N-dimethylformamide/sulfur, (1H-benzo[d]imidazol-2-yl)(phenyl)methanone was obtained; however, in the absence of sulfur, quinoxaline was obtained in 1,4-dioxane. A wide range of quinoxalines and (1H-benzo[d]imidazol-2-yl)(phenyl)methanones was obtained under mild conditions.
Copper-Catalyzed Cascade Cycloamination of α-Csp3-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines
Chen, Tengfei,Chen, Xun,Wei, Jun,Lin, Dongen,Xie, Ying,Zeng, Wei
, p. 2078 - 2081 (2016/06/01)
A copper-catalyzed cycloamination of α-Csp3-H bond of N-aryl ketimines with sodium azide has been developed. This methodology provides an efficient access to quinoxalines and features mild reaction conditions and readily available ketimines with diverse functional group tolerance.
Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted aldehydes and ketones with aryl diamines leading to quinoxalines using molecular oxygen as oxidant
Zhang, Chun,Xu, Zejun,Zhang, Liangren,Jiao, Ning
supporting information; experimental part, p. 5258 - 5262 (2012/08/08)
A novel Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted carbonyl compounds with aryl diamines leading to quinoxaline derivatives using molecular oxygen as oxidant has been developed. Six hydrogen dissociations involving 2 sp3 C-H bonds activation are realized under mild conditions in this approach. Plausible mechanism is proposed for this novel Et3N-catalyzed transformation on the basis of the aboratively designed mechanistic studies including the radical detection by EPR. 2012 Elsevier Science. All rights reserved.
2-Phenyl-(6(7)-R-substituted quinoxalines N-oxides. Synthesis, structure elucidation and antimicrobial activity
Loriga,Nuvole,Paglietti,Fadda,Zanetti
, p. 527 - 532 (2007/10/02)
A certain number of isomeric 2-phenylquinoxalines N-oxides bearing substituents at position 6/7 were prepared in order to investigate anti-microbial activity. The effect of some electron-withdrawing groups seem to increase an anti-Trichomonas vaginalis ac
