17492-65-8Relevant academic research and scientific papers
Facile Synthesis of Quinoxaline-2-thiol and Quinoxaline from α-Oxosulfines and o -Arylenediamines
Dong, Jun,Chen, Youwei,Huang, Xingcai
, p. 2616 - 2628 (2022/03/17)
A series of quinoxaline-2-thiols and quinoxalines were prepared in moderate to good yields from various phenacyl sulfoxides bearing 1-methyl-1H-tetrazole and o-arylenediamines. The proposed reaction mechanism involves generation of sulfines from the phenacyl sulfoxides bearing 1-methyl-1H-tetrazole through thermolysis elimination. Then, site-selective carbophilic addition of sulfines by o-arylenediamines, followed by elimination, intramolecular nucleophilic addition, and dehydration condensation. The current method provides a direct and simple strategy for the preparation of quinoxaline-2-thiols and quinoxalines.
Metal free C-H functionalization of diazines and related heteroarenes with organoboron species and its application in the synthesis of a CDK inhibitor, meriolin 1
Thatikonda, Thanusha,Singh, Umed,Ambala, Srinivas,Vishwakarma, Ram A.,Singh, Parvinder Pal
, p. 4312 - 4320 (2016/05/24)
Here, we report a metal-free cross-coupling reaction of diazines and related heteroarenes with organoboron species via C-H functionalization. The optimized conditions represent a metal-free method for the activation of aryl/heteroarylboronic acids, which undergo coupling with diazines and related heteroarenes. Optimized conditions also find application in the synthesis of a pyrimidine-based potent CDK inhibitor, meriolin1.
Chemoselective synthesis of quinoxalines and benzimidazoles by silica gel catalysis
Li, Chunmei,Zhang, Furen,Yang, Zhen,Qi, Chenze
supporting information, p. 5430 - 5433 (2014/12/11)
Treatment of nitroolefins and o-phenylenediamine with silica gel catalyst produced quinoxalines mainly in THF, but gave benzimidazoles efficiently in water. Such a solvent-dependent chemoselective reaction has prominent features of affording two cyclized products selectively with the same substrate, short reaction time, operational simplicity, as well as available starting materials and nontoxic catalysts. In addition, the scope and limitations were explored and a plausible reaction mechanism is proposed.
AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles
Wu, Degui,Zhang, Jian,Cui, Jianhai,Zhang, Wei,Liu, Yunkui
supporting information, p. 10857 - 10860 (2014/09/30)
A unique method for AgNO2-mediated direct nitration of the quinoxaline tertiary C-H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed. This protocol provides an efficient way to access quinoxaline containing nitroalkanes and nitriles depending on different substrate selection. the Partner Organisations 2014.
α-nitro epoxides in organic synthesis: Development of a one-pot organocatalytic strategy for the synthesis of quinoxalines
Ibrahim, Mohammad M.,Grau, Dominik,Hampel, Frank,Tsogoeva, Svetlana B.
, p. 1401 - 1405 (2014/03/21)
A new strategy for the synthesis of biologically active quinoxalines by using versatile α-nitro epoxides as starting compounds has been developed. In addition, the in situ organocatalytic epoxidation of electron-poor nitro olefins followed by condensation with 1,2-phenylenediamines to provide quinoxalines in one pot has been demonstrated. The reaction of easily accessible nitro olefins with the tBuOOH/1,8-diazabicycloundec-7-ene (TBHP/DBU) organocatalytic system gives rise to the corresponding α-nitro epoxides, which are suitable for subsequent reaction with 1,2-phenylenediamines under mild conditions to give quinoxaline heterocycles in up to 82 % yield. Copyright
α-Nitro Epoxides in Organic Synthesis: Development of a One-Pot Organocatalytic Strategy for the Synthesis of Quinoxalines
Ibrahim, Mohammad M.,Grau, Dominik,Hampel, Frank,Tsogoeva, Svetlana B.
, p. 1401 - 1405 (2015/10/05)
A new strategy for the synthesis of biologically active quinoxalines by using versatile α-nitro epoxides as starting compounds has been developed. In addition, the in situ organocatalytic epoxidation of electron-poor nitro olefins followed by condensation with 1,2-phenylenediamines to provide quinoxalines in one pot has been demonstrated.
Cu(II)-catalyzed synthesis of quinoxalines from o-phenylenediamines and nitroolefins
Chen, Yongxin,Li, Kangning,Zhao, Mingming,Li, Yuanjiao,Chen, Baohua
supporting information, p. 1627 - 1630 (2013/03/28)
An easy and efficient copper-catalyzed reaction for the synthesis of quinoxalines from o-phenylenediamines and nitroolefins is developed. This reaction could proceed well without additional base and be applied to various available substrates with a one-step synthetic procedure in moderate to good yields.
Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles
Cui, Dong-Mei,Zhuang, Dan-Wen,Chen, Ying,Zhang, Chen
experimental part, p. 860 - 865 (2011/08/05)
A gold-catalyzed oxidation of arylallenes to form α-diketones and aldehydes in good yields is presented. Further directed synthesis of quinoxalines and benzimidazoles, via the condensation of the resulting α-diketones and aldehydes with benzene-1,2-diamine, was achieved in high yields.
