5021-46-5Relevant academic research and scientific papers
Mechanically induced transition metal free C(sp2)-H arylation of quinoxalin(on)es with diaryliodonium salts and piezoelectric BaTiO3
Jiang, Jun,Song, Shengjie,Guo, JingJing,Zhou, Jiadi,Li, Jianjun
supporting information, (2022/05/04)
A transition metal free mechanically induced C(sp2)-H arylation of quinoxalin(on)es is described. In this study, diaryliodonium salts generate aryl radical by planetary ball milling, with the assist of piezoelectric material BaTiO3. A broad range of functional groups are tolerated to give products in moderate to good yields via radical mechanism.
Silica supported dodecatungstophosphoric acid (DTP/SiO2): An efficient and recyclable heterogeneous catalyst for rapid synthesis of quinoxalines
Hebade, Madhav J.,Deshmukh, Tejshri R.,Dhumal, Sambhaji T.
, p. 2510 - 2520 (2021/06/17)
A facile synthesis of quinoxalines by the cyclocondensation of substituted phenacyl bromides with o-pheneylenediamines using silica-supported dodecatungstophosphoric acid (DTP/SiO2) as a recyclable heterogeneous catalyst is unveiled in this res
A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst
Vasu, Amrutham,Naresh, Mameda,Krishna Sai, Gajula,Divya Rohini, Yennamaneni,Murali, Boosa,Ramulamma, Madasu,Ramunaidu, Addipilli,Narender, Nama
, p. 9439 - 9446 (2021/12/09)
This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is
Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines
Sofi, Firdoos Ahmad,Sharma, Rohit,Rawat, Ravi,Chakraborti, Asit K.,Bharatam, Prasad V.
supporting information, p. 4569 - 4573 (2021/03/22)
Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction ofortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.
Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives
Che, Tong,Kang, Hua-Jie,Peng, Dongming,Shu, Bing,Song, Jia-Lin,Wang, Xiao-Tong,Xie, Hui,Zhang, Luyong,Zhang, Shang-Shi,Zhong, Mei
supporting information, (2020/06/25)
A synthetic method for quinoxaline derivatives from the [4+2] annulation of β-keto sulfoxonium ylides and o-phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional-group compatibility. Moreover, this cyclization strategy was successfully applied in late-stage modification for structurally complex bioactive compounds.
Novel green synthesis method for efficiently synthesizing quinoxaline derivative through transition metal catalyzed carbene insertion/cyclization reaction
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Paragraph 0014, (2020/05/09)
The invention discloses a novel green synthesis method for efficiently synthesizing a C-N bond and a quinoxaline derivative through a transition metal catalyzed carbene insertion/cyclization reactionby taking pure water as a solvent and sulfur ylide as a carbene donor. Compared with the traditional method, the method has the advantages that the raw materials are easy to obtain, the steps are simple, the use of toxic organic solvents is avoided and the method is a mild, quick, simple, convenient, effective and environment-friendly method for preparing the quinoxaline mother ring and has a wideapplication prospect.
Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
Xu, Yingying,Huang, Xin,Lv, Guanghui,Lai, Ruizhi,Lv, Songyang,Li, Jianglian,Hai, Li,Wu, Yong
supporting information, p. 4635 - 4638 (2020/07/04)
Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.
Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls
Dubovtsev, Alexey Yu.,Shcherbakov, Nikolay V.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
, p. 745 - 757 (2020/02/04)
2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.
Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach
Bartolomeu, Aloisio De A.,Brocksom, Timothy J.,De Oliveira, Kleber T.,No?l, Timothy,Silva, Rodrigo C.
, (2019/08/26)
A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96percent. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the ortho, meta, or para positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.
An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives
Bhargava, Sangeeta,Soni,Rathore, Deepti
, (2019/08/08)
A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship between the catalytic activity and acidity was discussed. It was also found that among the all ILs, [Bmim]CF3SO3 was the most effective, eco-friendly and less expensive solvent and catalyst for the above etiquette. This method is of significant value due to the eco-friendly nature of ionic liquid and non usage of separate catalyst to drive the reaction forward. The protocol proves to be efficient and environmentally benign in terms of good to excellent yields, low reaction times, simple work-up, ease of recovery, and reusability of ionic liquid for six times.
