17286-62-3Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling of 2-chloroquinoxaline N-Oxides with arylboronic acids
Maichrowski, Jan,Huebner, Eike G.,Kaufmann, Dieter E.
, p. 8185 - 8196 (2013)
A selection of 2-chloro-substituted O-alkylquinoxaline N-oxides, easily accessible by the one-step annulation reaction of 4-fluoroaniline with 1,1,2-trichloro-2-nitroethylene and subsequent O-alkylation, was arylated at the chloronitrone unit in yields up to 96 %. This first efficient Pd-catalyzed Suzuki-Miyaura reaction of chloroquinoxaline N-oxides with arylboronic acids led to new 2-arylquinoxaline N-oxides. The scope and limitations of this arylation reaction were investigated, and the role of some sterically demanding boronic acids in the cross-coupling reaction was evaluated by means of DFT calculations. Additionally, the Pd-catalyzed C-arylation of the amide unit of selected quinoxalinone derivatives was accomplished. For the first time the chloronitrone unit of 2-chloroquinoxaline N-oxides was arylated with arylboronic acids under Suzuki-Miyaura cross-coupling conditions in good to very good yields. The scope and limitations of the applied protocols were investigated as well as the dependency of the yield of the reaction on the steric bulk of the arylboronic acid by means of DFT calculations. Copyright
Manganese(IV) dioxide-catalyzed synthesis of quinoxalines under microwave irradiation
Kim, So Yeon,Park, Kang Hyun,Chung, Young Keun
, p. 1321 - 1323 (2005)
We synthesize quinoxalines, catalyzed by manganese(IV) dioxide, from a variety of α-hydroxyketones followed by trapping with aromatic or aliphatic 1,2-diamines without using a solvent, within one minute under microwave irradiation. The Royal Society of Chemistry 2005.
Silica nanosphere–graphene oxide (SiO2–GO) hybrid catalyzed facile synthesis of functionalized quinoxaline derivatives
Shitre, Praveen V.,Harale, Rajkumar R.,Sathe, Bhaskar R.,Shingare, Murlidhar S.
, p. 829 - 841 (2017)
Abstract: Herein, fabrication of spherical SiO2 nanoparticles (5?±?0.2?nm) with uniform size is followed by their homogeneous distribution on graphene oxide (SiO2–GO) by using a simple in situ one-step method. These as synthesized ca
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
Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source
Chen, Jingchao,Fan, Baomin,Guo, Qi,Lu, Guangfu,Shen, Guoli,Tang, Yan,Wu, Shiyuan,Yang, Xuemei,Zhu, Yuanbin
, (2021/12/27)
A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.
NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy
Wang, Yan-Bing,Shi, Linlin,Zhang, Xiaojie,Fu, Lian-Rong,Hu, Weinan,Zhang, Wenjing,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
, p. 947 - 958 (2021/01/14)
A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.
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
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.
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.
