3885-38-9Relevant academic research and scientific papers
Improved synthesis of substituted quinoxalines from new N=N-polymerbound 1,2-diaza-1,3-butadienes
Attanasi, Orazio A.,De Crescentini, Lucia,Filippone, Paolino,Mantellini, Fabio,Santeusanio, Stefania
, p. 1183 - 1185 (2003)
The first general protocol for the preparation of different N=N-polymer-bound 1,2-diaza-1,3-butadienes is reported. The utility of these supported reagents in the solid-phase in the preparation of 3-methyl quinoxaline-2-carboxylates by reaction with aroma
Method for synthesizing quinoxaline compounds through double-protein catalytic cascade reaction
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Paragraph 0052-0058, (2021/01/25)
The invention relates to the technical field of biological catalytic synthesis and particularly discloses a method for synthesizing quinoxaline compounds by a double-protein catalytic cascade reaction. The method comprises the steps as follows: a beta-keto ester compound, substituted o-phenylenediamine and methylphenylsulfonyl azido are taken as reactants to be dissolved in a solvent, a catalyst and a surfactant are added, the mixture is stirred to react to produce a product, and the product is sequentially dried, concentrated and purified, wherein the solvent is water, and the catalyst is procine pancreaslipase (PPL) and hemoglobin from bovine blood (HbBv). The process is convenient, a heme protein catalytic carbene reaction and a lipase protein catalytic reaction are coupled to constructa green method for synthesizing quinoxaline compound by double proteins by a one-pot method, the target product can be rapidly and conveniently synthesized, meanwhile, synthesis is completed in water, and the problems that the existing quinoxaline compound preparation method comprises more synthesis steps and is not green and environmentally friendly enough are solved.
Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors
Platte, Simon,Korff, Marvin,Imberg, Lukas,Balicioglu, Ilker,Erbacher, Catharina,Will, Jonas M.,Daniliuc, Constantin G.,Karst, Uwe,Kalinin, Dmitrii V.
, p. 3672 - 3690 (2021/08/07)
Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.
A dual-protein cascade reaction for the regioselective synthesis of quinoxalines
Li, Fengxi,Li, Zhengqiang,Tang, Xuyong,Wang, Chunyu,Wang, Lei,Wang, Zhi,Xu, Yaning
supporting information, p. 3900 - 3904 (2020/06/08)
In this work, an efficient dual-protein (lipase and hemoglobin) system was successfully constructed for the regioselective synthesis of quinoxalines in water. A set of quinoxalines were obtained in high yields under optimal reaction conditions. This dual-protein method exhibited a regioselectivity higher than those of previously reported methods. This study not only provides a green and mild strategy for the synthesis of quinoxalines but also expands the application of lipase and hemoglobin in organic synthesis.
Isobutyl Nitrite-Mediated Synthesis of Quinoxalines through Double C?H Bond Amination of N-Aryl Enamines
Jiao, Yan-Xiao,Wei, Lin-Su,Zhao, Chun-Yang,Wei, Kai,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
supporting information, p. 4446 - 4451 (2018/10/20)
An efficient and metal-free double C?H bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key β-imino oxime ester intermediate. A quinoxaline derivative could be prepared from β-carbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps. (Figure presented.).
One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid
De Andrade, Vitor S. C.,De Mattos, Marcio C. S.
, p. 4867 - 4874 (2018/12/13)
A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which
Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines
Jiao, Yan-Xiao,Wu, Ling-Ling,Zhu, Hai-Miao,Qin, Jiang-Ke,Pan, Cheng-Xue,Mo, Dong-Liang,Su, Gui-Fa
, p. 4407 - 4414 (2017/04/28)
Diverse functionalized quinoxalines were synthesized in good yields from arylamines and readily available β-keto oximes through condensation and metal-free N-arylation. The reaction was compatible with various functional groups, such as halides, cyano, and esters. A mechanism was proposed based on the experimental results. These quinoxalines were easily obtained on a gram scale and converted to various useful scaffolds. Compound LASSBio-1022 was prepared in 83% yield in two steps.
Iron-Catalyzed Annulation of 1,2-Diamines and Diazodicarbonyls for Diverse and Polyfunctionalized Quinoxalines, Pyrazines, and Benzoquinoxalines in Water
Pandit, Rameshwar Prasad,Kim, Sung Hong,Lee, Yong Rok
, p. 3586 - 3599 (2016/11/25)
A novel and facile iron-catalyzed tandem annulation of o-phenylenediamines and diazocarbonyls in water for the construction of polyfunctionalized quinoxalines has been developed. The key strategy includes the one-pot domino N?H insertion, cyclization, and
2,3-di-substituted quinoxaline derivatives method for the preparation of
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Paragraph 0043; 0044; 0066, (2016/11/24)
The invention discloses a novel preparation method for 2,3-disubstituted quinoxaline derivatives. After arylamine and a 1,3-dicarbonyl-2-oxime compound serving as raw materials are condensed, cyclization is performed by using electrophilic substitution reaction of nitrogen positive ions in molecules, so that 'condensation-cyclization' reactions are skillfully linked together, and the 2,3-disubstituted quinoxaline derivatives having different substituent groups on benzene rings are obtained by a two-step one-kettle method. Compared with the traditional synthetic method, the method has the advantages that the raw materials are cheap and readily available; intermediate products do not need to be treated in the process, so that the synthesis steps are simplified; particularly, substitution on the benzene rings can be carried out by using arylamine compounds in many different ways, so that diversity of product structures is realized, and deep study on the quinoxaline derivatives is facilitated. 18 unreported new compounds are also obtained by using the method disclosed by the invention.
Quinoxaline synthesis in novel tandem one-pot protocol
Anil Kumar,Madhav,Harsha Vardhan Reddy,Nageswar
supporting information; experimental part, p. 2862 - 2865 (2011/06/21)
A variety of quinoxalines were synthesized via tandem one-pot procedure for the first time in water medium. The key strategy was the in situ preparation of α-halo-β-keto esters by the reaction of N-bromo succinimide with β-keto esters and further condensa
