494-21-3Relevant articles and documents
A One-pot Synthesis of Cyclic Pyrido[1,2-a]quinoxaline Phosphate, a New Molecule of Biological Importance from a Quinoxaline Derivative of Sugar
Goswami, Shyamaprosad,Adak, Avijit Kumar
, p. 678 - 679 (2003)
A five membered cyclic pyrido[1,2-a]quinoxaline phosphate has been first synthesized in one step in a good yield by phosphorylation of the quinoxaline derivative of sugar 1a with (PhO)P(O)Cl2. Phosphorylation of the tetrols (1a and 1b) and the diol acetals with other phosphorylating agents, however, affords a dehydration product 2-(2-furyl)quinoxaline.
Transition Metal-Free Heteroarylation of Quinoxaline: Construction of Heteroaryl-Fused Phenazines by Oxidative Coupling
U?ar, Sefa,Da?tan, Arif
, p. 15502 - 15513 (2020/11/30)
A concise method for the construction of heteroaryl-fused phenazines was developed via PIFA-BF3·Et2O-mediated oxidative coupling of di-heteroarylated quinoxalines for the first time. Synthesis of mono- and di-heteroarylation of quinoxaline was performed effectively using only LiTMP reagent under transition metal-free conditions and without the use of halogen-containing starting compounds. In addition, nonsymmetrical di-heteroarylated quinoxalines were synthesized through reheteroarylation of mono-heteroarylated quinoxalines in the same way. Oxidation of the saturated compounds formed after heteroarylation was easily accomplished with iodine. The UV-vis absorption and fluorescence features of some compounds were examined.
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.
Investigation and Application of Amphoteric α-Amino Aldehyde: An in Situ Generated Species Based on Heyns Rearrangement
Li, Guangxun,Tang, Ling,Liu, Hongxin,Wang, Yingwei,Zhao, Gang,Tang, Zhuo
, p. 4526 - 4529 (2016/09/28)
In situ generation of the reactive amphoteric α-amino aldehyde with simple α-hydroxy ketones and phenylamine via Heyns rearrangement was proven to be feasible. Metal-free domino reactions based on this reactive intermediate were effectively used to afford important N-heterocycles including polysubstituted pyrroles, indoles, and quinoxalines conveniently. A simple starting material, water as the only byproduct, and diversity of the useful products will make this method greatly attractive for pharmaceutics.
Copper-Catalyzed Cascade Cycloamination of α-Csp3-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines
Chen, Tengfei,Chen, Xun,Wei, Jun,Lin, Dongen,Xie, Ying,Zeng, Wei
, p. 2078 - 2081 (2016/06/01)
A copper-catalyzed cycloamination of α-Csp3-H bond of N-aryl ketimines with sodium azide has been developed. This methodology provides an efficient access to quinoxalines and features mild reaction conditions and readily available ketimines with diverse functional group tolerance.
One-step approach for the synthesis of functionalized quinoxalines mediated by T3P-DMSO or T3P: Via a tandem oxidation-condensation or condensation reaction
Harsha, Kachigere B.,Rangappa, Kanchugarkoppal S.
, p. 57154 - 57162 (2016/07/07)
An easy and efficient propylphosphonic anhydride (T3P)-DMSO or T3P mediated oxidation-condensation or condensation reaction for the synthesis of quinoxalines derived from the interaction of different arrays of condensing partners with ortho-phenylene diamines (o-PDs) under simple and mild reaction conditions in one step has been reported for the first time.
I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization
Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Murugan, Kaliyappan,Chaskar, Atul C.
, p. 5580 - 5590 (2015/02/05)
One-pot, atom-economic synthesis of quinoxalines has been achieved through generation of arylglyoxal from easily available ethylarenes, ethylenearenes and ethynearenes, and subsequent condensation with o-phenylenediamines. Catalytic I2 with TBHP as an oxidant in DMSO is the system of choice for this domino reaction involving C-H functionalization/oxidative cyclization. This metal-free, mechanistically distinct and functional group tolerant tandem approach could be a powerful complement to traditional approaches for the synthesis of quinoxalines. This journal is
A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3- b ]pyrazines
Lassagne, Frédéric,Chevallier, Floris,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence,Domingo, Luis R.
, p. 2680 - 2689 (2015/09/01)
Ammonium bifluoride was efficiently used at a 0.5 mol% loading to catalyze the cyclocondensation of 1,2-arylenediamines with 1,2-dicarbonyl compounds at room temperature in methanol-water to give quinoxalines or pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by the reaction of arylglyoxals with 3-methylbenzene-1,2-diamine or pyridine-2,3-diamine, respectively. An analysis of the density functional theory reactivity indices explained the catalytic role of ammonium bifluoride.
Regioselective Metal-Free Cross-Coupling of Quinoline N -Oxides with Boronic Acids
Bering, Luis,Antonchick, Andrey P.
, p. 3134 - 3137 (2015/06/30)
A novel and operationally simple one-step C-H bond functionalization of quinoline N-oxides to 2-substituted quinolines was developed. This approach enables the regioselective functionalization under external oxidant- and metal-free conditions. The developed transformation represents the first application of the Petasis reaction in functionalization of heterocycles.
Copper-catalyzed domino synthesis of 2-imino-1H-imidazol-5(2H)-ones and Quinoxalines involving C-C bond cleavage with a 1,3-dicarbonyl unit as a leaving group
Yang, Yan,Ni, Fan,Shu, Wen-Ming,Wu, An-Xin
supporting information, p. 11776 - 11782 (2014/10/15)
Although 2-imino-1H-imidazol-5(2H)-ones have important biological activities in metabolism, their synthesis has rarely been investigated. Quinoxalines as privileged scaffolds in medicinal chemistry have been extensively investigated, but the development of novel and efficient synthetic methods remains very attractive. Herein, we have developed two copper-catalyzed domino reactions for the synthesis of 2-imino-1H-imidazol-5(2H) -ones and quinoxalines involving C-C bond-cleavage with a 1,3-dicarbonyl unit as a leaving group. The domino sequence for the synthesis of 2-imino-1H-imidazol- 5(2H)-ones includes aza-Michael addition, intramolecular cyclization, C-C bond-cleavage, 1,2-rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza-Michael addition, intramolecular cyclization, elimination reaction, and C-C bond-cleavage reaction. The two domino reactions have significant advantages including high efficiency, mild reaction conditions, and high tolerance of various functional groups.
