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
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.
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
