- A new ruthenium-catalyzed approach for quinoxalines from o-phenylenediamines and vicinal-diols
-
o-Phenylenediamines react with an array of vicinal-diols in diglyme in the presence of a catalytic amount of a ruthenium catalyst along with KOH to afford the corresponding quinoxalines in good yields.
- Cho, Chan Sik,Oh, Sung Gi
-
-
Read Online
- Mechanically induced transition metal free C(sp2)-H arylation of quinoxalin(on)es with diaryliodonium salts and piezoelectric BaTiO3
-
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.
- Jiang, Jun,Song, Shengjie,Guo, JingJing,Zhou, Jiadi,Li, Jianjun
-
supporting information
(2022/05/04)
-
- Direct C-2 arylation of quinoxaline with arylhydrazine salts as arylation reagents
-
A transition metal-free synthesis of 2-arylquinoxaline is achieved by using arylhydrazine salt as an aryl radical arylation reagent and air as an oxidant in the presence of K2CO3. This protocol features metal-free, no additives, mild reaction conditions, environment friendly, and can be used to construct biologically active molecules containing 2-phenylquinoxaline structure.
- Chen, Yi,Miao, Jing,Tang, Lei,Wang, Bing,Wang, Cong,Wang, Haibo,Wang, Jianta,Wang, Xing,Zhang, Jiquan,Zhu, Gaofeng
-
supporting information
(2022/03/15)
-
- Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
-
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.
- Xu, Yingying,Huang, Xin,Lv, Guanghui,Lai, Ruizhi,Lv, Songyang,Li, Jianglian,Hai, Li,Wu, Yong
-
p. 4635 - 4638
(2020/07/04)
-
- Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives
-
A synthetic method for quinoxaline derivatives from the [4+2] annulation of β-keto sulfoxonium ylides and o-phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional-group compatibility. Moreover, this cyclization strategy was successfully applied in late-stage modification for structurally complex bioactive compounds.
- Che, Tong,Kang, Hua-Jie,Peng, Dongming,Shu, Bing,Song, Jia-Lin,Wang, Xiao-Tong,Xie, Hui,Zhang, Luyong,Zhang, Shang-Shi,Zhong, Mei
-
supporting information
(2020/06/25)
-
- One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N-Bromosuccinimide
-
N-bromosuccinimide (NBS)-mediated one-pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N-arylbenzamidines and o-phenylenediamines, respectively, in a water:1,4-dioxane mixture. The reaction involves formation of an α-bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with the N-arylbenzamidine and o-phenylenediamine. Use of an inexpensive NBS as a bromine source as well as an oxidant, water as a solvent and readily available starting materials makes this protocol environmentally benign and economically viable. Substituted imidazoles and quinoxalines were obtained in good to excellent yields with wide functional group compatibility. (Figure presented.).
- Pardeshi, Sachin D.,Sathe, Pratima A.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
-
supporting information
p. 4217 - 4226
(2017/12/07)
-
- Ambient benzotriazole ring opening through intermolecular radical addition to vinyltriazole
-
Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.
- Su, Yijin,Petersen, Jeffrey L.,Gregg, Tesia L.,Shi, Xiaodong
-
p. 1208 - 1211
(2015/03/14)
-
- I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization
-
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
- Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Murugan, Kaliyappan,Chaskar, Atul C.
-
p. 5580 - 5590
(2015/02/05)
-
- An iodobenzene-catalysed domino route toward quinoxaline derivatives from simple ketones and o-phenylenediamines in one pot
-
An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation. Website
- Li, Xiaoqing,Zhou, Can,Hu, Zhiyan,Xu, Xiangsheng
-
p. 579 - 581
(2013/10/22)
-
- Palladium-catalyzed cross-coupling reaction of functionalized aryl- and heteroarylbismuthanes with 2-halo(or 2-Triflyl)azines and -diazines
-
The palladium-catalyzed cross-coupling of highly functionalized organobismuthanes with 2-halo(or 2-triflyl)pyridines, -pyrimidines, -pyrazines, and -pyridazines is reported. The reaction tolerates numerous functional groups, including aldehydes. The synthesis of a shelf-stable (formylphenyl)bismuth reagent and its use in a cross-coupling reaction is also described. The palladium-catalyzed cross-coupling of highly functionalized organobismuthanes with 2-halo(or 2-triflyl)pyridines, -pyrimidines, -pyrazines, and -pyridazines is reported. The reaction tolerates numerous functional groups, including aldehydes. The synthesis of a shelf-stable (formylphenyl)bismuth reagent and its use in cross-coupling reactions is also described. Copyright
- Petiot, Pauline,Gagnon, Alexandre
-
supporting information
p. 5282 - 5289
(2013/09/02)
-
- Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted aldehydes and ketones with aryl diamines leading to quinoxalines using molecular oxygen as oxidant
-
A novel Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted carbonyl compounds with aryl diamines leading to quinoxaline derivatives using molecular oxygen as oxidant has been developed. Six hydrogen dissociations involving 2 sp3 C-H bonds activation are realized under mild conditions in this approach. Plausible mechanism is proposed for this novel Et3N-catalyzed transformation on the basis of the aboratively designed mechanistic studies including the radical detection by EPR. 2012 Elsevier Science. All rights reserved.
- Zhang, Chun,Xu, Zejun,Zhang, Liangren,Jiao, Ning
-
supporting information; experimental part
p. 5258 - 5262
(2012/08/08)
-
- A recyclable copper catalysis in quinoxaline synthesis from α-hydroxyketones and o-phenylenediamines
-
o-Phenylenediamines react with α-hydroxyketones in toluene at 100 °C in the presence of a catalytic amount of a copper catalyst along with MS 4A under O2 atmosphere to afford the corresponding quinoxalines in high yields. The catalytic system c
- Cho, Chan Sik,Ren, Wen Xiu
-
experimental part
p. 3215 - 3217
(2010/01/06)
-
- Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
-
The reaction of 2-aroylquinoxalines (1) with sodium hydroxide in dimethyl sulfoxide (DMSO) was found to result in aryl migration, fission of the C2-C=O bond, and addition of DMSO to the C=O group, giving 2-arylquinoxalines (2), quinoxaline (4), aroic acids (5), and α-aryl-α-(methylsulfinylmethyl)-2-quinoxalinemethanols (6).Compounds 6 could be separatedinto two racemates, (αR*,SR*)-6, and (αR*,SS*)-6.In order to establish the generality of the aryl migration, other aroylated aromatic heterocycles were examined. 3-Aroylpyridopyrazines (7) and 1-benzoyl-4-isoquinolinecarbonitrile (10) both underwent similar aryl migration to give 3-arylpyridopyrazines (14) and 1-phenyl-4-isoguinolinecarbonitrile (18), respectively.On the other hand, the reaction of 1-benzoylisoquinoline (9) and 2-benzoilquinoline (11) resulted not in migration, but in the addition of DMSO to give 1-isoquinolinemethanol (16) and 2-quinolinemethanol derivatives (20), respectively.In the case of 1-benzoylphtalazine (8), migration did not occur, but instead 4-benzoyl-1(2H)-phthalazinone (15) was formed.Keywords - 2-aroylquinoxaline; 2-arylquinoxaline; 2-quinoxalinemethanol; aryl migration; racemate; 3-arylpyridopyrazine; 1-isoquinolinemethanol; 2-quinolinemethanol; 1-phenyl-4-isoquinolinecarbonitrile; 4-benzoyl-1(2H)-phthalazinone
- Higashino, Takeo,Takemoto, Masumi,Tanji, Ken-Ichi,Iijima, Chihoko,Hayashi, Eisaku
-
p. 4193 - 4201
(2007/10/02)
-