1057221-63-2Relevant academic research and scientific papers
Transition Metal-Free Direct C-3 Arylation of Quinoxalin-2(1H)-ones with Arylamines under Mild Conditions
Yuan, Jinwei,Liu, Shuainan,Qu, Lingbo
, p. 4197 - 4207 (2017)
A transition metal-free direct C-3 arylation of quinoxalin-2(1H)-ones with arylamines has been explored. This reaction proceeded smoothly through a radical process under mild conditions and produced the desired arylation products in good yields. The reactions proceeded efficiently with a broad range of substrates and functional group tolerance. (Figure presented.).
A niobium-catalyzed coupling reaction of α-keto acids with: Ortho -phenylenediamines: Synthesis of 3-arylquinoxalin-2(1 H)-ones
Ebersol, Camila,Rocha, Nicole,Penteado, Filipe,Silva, Márcio S.,Hartwig, Daniela,Lenard?o, Eder J.,Jacob, Raquel G.
, p. 6154 - 6160 (2019)
A general methodology to access valuable 3-arylquinoxalin-2(1H)-ones was developed, by the reaction of α-keto acids with ortho-phenylenediamines in the presence of ammonium niobium oxalate (ANO) as a catalyst. The reactions were conducted in only 10 min under ultrasonic irradiation as an alternative energy source, affording water as the only co-product. A total of twenty-three different 3-arylquinoxalin-2(1H)-ones were selectively obtained in good to excellent yields by this atom-efficient protocol. Additionally, 1H-15N HMBC experiments were used to reveal the regioisomerism of the obtained products.
α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
, p. 14866 - 14882 (2021/10/25)
A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
K2S2O8 mediated C-3 arylation of quinoxalin-2(1H)-ones under metal-, photocatalyst- And light-free conditions
Dutta, Nibedita Baruah,Bhuyan, Mayurakhi,Baishya, Gakul
, p. 3615 - 3624 (2020/02/06)
Two facile and effective C-3 arylation protocols of quinoxalin-2(1H)-ones with arylhydrazines and aryl boronic acids respectively via free radical cross-coupling reactions under metal-, photocatalyst- and light-free conditions have been unveiled. K2
Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis
Yu, Qing,Zhang, Yating,Wan, Jie-Ping
supporting information, p. 3436 - 3441 (2019/06/24)
The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.
Preparation method of quinoxalinone derivatives
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Paragraph 0077-0080, (2019/12/02)
The invention belongs to the field of organic synthetic chemistry. The invention relates to a preparation method of quinoxalinone derivatives. Specifically, a covalent organic framework material 2D-COF-1 is used as a photocatalyst; and the quinoxaline-2 (
Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach
Jiang, Yang-ye,Dou, Gui-yuan,Zhang, Luo-sha,Xu, Kun,Little, R. Daniel,Zeng, Cheng-chu
, p. 5170 - 5175 (2019/11/13)
Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).
Synthesis of 9,10-substituted 3,4,10,10a-tetrahydro-2H,9H-1-oxa-4a,9- diazaphenanthrenes by reductive cyclization method
Rajachandrasekhar,Hariprasad,Venugopala Rao,Venkataiah,Dubey
, p. 3161 - 3165 (2014/07/22)
Commercially available o-phenylenediamine (1) was treated with methyl α-bromo-α-aryl acetate to obtain 3-aryl-3,4-dihydro-1Hquinoxalin- 2-one (2). The latter was reacted with benzyl bromide to obtain 4-benzyl-3-aryl-3,4-dihydro-1H-quinoxalin-2-one (3). Tr
The first general, highly enantioselective lewis base organocatalyzed hydrosilylation of benzoxazinones and quinoxalinones
Xue, Zhou-Yang,Jiang, Yan,Peng, Xiao-Zhi,Yuan, Wei-Cheng,Zhang, Xiao-Mei
supporting information; experimental part, p. 2132 - 2136 (2010/11/04)
The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysis that are readily accessible from (1S,2R)-ephedrine and (1R,2S)-ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.
