17286-62-3Relevant articles and documents
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
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
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
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.
