- Transition Metal-Free Heteroarylation of Quinoxaline: Construction of Heteroaryl-Fused Phenazines by Oxidative Coupling
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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.
- U?ar, Sefa,Da?tan, Arif
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- Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives
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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
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supporting information
(2020/06/25)
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- Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
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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
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supporting information
p. 4635 - 4638
(2020/07/04)
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- Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls
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2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.
- Dubovtsev, Alexey Yu.,Shcherbakov, Nikolay V.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
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p. 745 - 757
(2020/02/04)
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- Synthesis and characterization of linear 1,4-diazine-triphenylamine–based selective chemosensors for recognition of nitroaromatic compounds and aliphatic amines
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Novel 1,4-diazine-based dyes of the D–π–A type, possessing triphenylamine as an electron-donating group, have been developed. Fluorescence studies have demonstrated that emission of these fluorophores is sensitive towards different nitroaromatic compounds and aliphatic amines, both in solutions and in a vapor phase. Moreover, these compounds can be considered as “naked-eye” fluorescent probes for solution polarity because they possess pronounced solvatochromic properties. Therefore, these compounds have to be regarded as potential multifunctional chemosensors for monitoring hazardous organic substances.
- Baranova, Anna A.,Charushin, Valery N.,Chupakhin, Oleg N.,Chuvashov, Roman D.,Khokhlov, Konstantin O.,Kvashnin, Yuriy A.,Makarova, Nadezhda I.,Metelitsa, Anatoly V.,Rusinov, Gennady L.,Schapov, Il'ya E.,Shchepochkin, Aleksandr V.,Verbitskiy, Egor V.,Vetrova, Elena V.,Yakovleva, Yuliya A.,Zhilina, Ekaterina F.
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- (DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki-Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls
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The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki-Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described.
- Sawatzky, Ryan S.,Stradiotto, Mark
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p. 799 - 804
(2018/01/11)
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- Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones
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Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.
- Sahoo, Subas Chandra,Nath, Utpal,Pan, Subhas Chandra
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p. 4434 - 4438
(2017/08/23)
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- Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines
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A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily scaled up and applied to the synthesis of biologically active molecules bearing a quinoxaline structural scaffold.
- Gopalaiah, Kovuru,Saini, Anupama,Chandrudu, Sankala Naga,Rao, Devarapalli Chenna,Yadav, Harsh,Kumar, Binay
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p. 2259 - 2268
(2017/03/20)
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- Elemental sulfur mediated synthesis of benzoxazoles, benzothiazoles and quinoxalines: Via decarboxylative coupling of 2-hydroxy/mercapto/amino-anilines with cinnamic acids
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An easy and practical method has been developed for the synthesis of 2-benzylbenzoxazoles and 2-benzylbenzothiazoles using sulfur mediated decarboxylative coupling of cinnamic acids with 2-hydroxyanilines and 2-mercaptoanilines respectively under metal- and solvent-free conditions. However, the reaction of 2-aminoanilines with cinnamic acids leads to the formation of 2-arylquinoxalines under the same set of reaction conditions. The transformation is versatile and compatible with a number of functional groups.
- Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Kumar, Saurabh,Singh, Rahul,Singh, Neetu,Kumar, Promod,Singh, Krishna Nand
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p. 81013 - 81016
(2016/09/09)
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- Copper-Catalyzed Cascade Cycloamination of α-Csp3-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines
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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.
- Chen, Tengfei,Chen, Xun,Wei, Jun,Lin, Dongen,Xie, Ying,Zeng, Wei
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p. 2078 - 2081
(2016/06/01)
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- One-step approach for the synthesis of functionalized quinoxalines mediated by T3P-DMSO or T3P: Via a tandem oxidation-condensation or condensation reaction
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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.
- Harsha, Kachigere B.,Rangappa, Kanchugarkoppal S.
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p. 57154 - 57162
(2016/07/07)
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- Synthesis of 2-arylquinoxalines: Triarylstibane-catalyzed oxidative cyclization of α-hydroxy ketones with 1,2-diamines under aerobic conditions
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The reaction of α-hydroxy ketones with 1,2-diamines in the presence of triphenylstibane (10 mol%) as catalyst led to the formation of 2-arylquinoxalines in moderate to good yield under aerobic conditions. This reaction is the first example of oxidative cy
- Matsumura, Mio,Takada, Rie,Ukai, Yuu,Yamada, Mizuki,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
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- I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization
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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.
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p. 5580 - 5590
(2015/02/05)
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- A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3- b ]pyrazines
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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.
- Lassagne, Frédéric,Chevallier, Floris,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence,Domingo, Luis R.
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p. 2680 - 2689
(2015/09/01)
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- I2/Cu-mediated self-sorting domino reaction of aryl β-ketoesters into symmetrical 2-carboalkoxy-1,4-enediones: Application to synthesis of pyrazine, β-carboline and quinoxalines
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A self-sorting domino reaction of aryl β-ketoesters into symmetrical 1,4-enediones is reported by an I2/Cu system. The reaction proceeds through tandem iodination, self-dimerization and Krapcho dealkoxycarbonylation in one pot under open air condition. Further, 1,4-enediones were successfully employed for the synthesis of bioactive pyrazine, β-carboline and quinoxalines via aza-Michael addition, intramolecular cyclization and C-C bond cleavage of 1,3-dicarbonyl unit under mild reaction condition. This journal is
- Satish, Gandhesiri,Ilangovan, Andivelu
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p. 46163 - 46172
(2015/06/08)
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- Saccharin as an organocatalyst for quinoxalines and pyrido[2,3-b[pyrazines Syntheses
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A room-temperature procedure using saccharin as catalyst has been described for the cyclocondensation of different 1,2-arylenediamines with various 1,2-dicarbonyl compounds, yielding either quinoxalines or pyrido[2,3-b] pyrazines. The reactions proceed in very short reaction times in methanol, and the target heterocycles are isolated in quantitative yields after addition of water, filtration, and drying. Substituted pyrido[2,3-b]pyrazines can also be reached regioselectively by reacting α-ketoaldehydes with 2,3-diaminopyridine. Taylor and Francis Group, LLC.
- Lassagne, Frederic,Chevallier, Floris,Mongin, Florence
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supporting information
p. 141 - 149
(2013/11/06)
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- An iodobenzene-catalysed domino route toward quinoxaline derivatives from simple ketones and o-phenylenediamines in one pot
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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
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p. 579 - 581
(2013/10/22)
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- Palladium-catalyzed cross-coupling reaction of functionalized aryl- and heteroarylbismuthanes with 2-halo(or 2-Triflyl)azines and -diazines
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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
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supporting information
p. 5282 - 5289
(2013/09/02)
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- Sodium dodecylsulfate induced synthesis of quinoxalines
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A simple and efficient sodium dodecylsulfate (SDS) induced method for the synthesis of quinoxalines in excellent yields in water at room temperature by the reaction of phenacyl bromide and o-phenylene diamines has been developed. Simple reaction conditions, wide compatibility and high yields are the advantages of this protocol.
- Emmadi, Narender Reddy,Atmakur, Krishnaiah
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p. 1500 - 1504
(2014/01/23)
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- Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines
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A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H 2O.
- Lian, Mi,Li, Qi,Zhu, Yanping,Yin, Guodong,Wu, Anxin
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p. 9598 - 9605
(2012/11/07)
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- CeCl3·7H2O-catalyzed synthesis of quinoxaline derivatives in liquid PEG-400
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A mild and efficient route for the synthesis of quinoxaline derivatives utilizing cerium chloride heptahydrate (CeCl3·7H2O) as a novel catalyst in poly(ethylene glycol) (PEG-400) under mild conditions was described.
- Wu, Fang-Wen,Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Chen, Ling-Ching
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experimental part
p. 2313 - 2320
(2011/11/06)
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- SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS
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A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.
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Page/Page column 53, 57-58
(2010/04/27)
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- Hypervalent iodine(iii) sulfonate mediated synthesis of quinoxalines in liquid peg-400
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PEG-400[poly(ethylene glycol-400)] is used as a "green" recyclable solvent in the one-pot synthesis of quinoxalines by reaction with aryl ketones, hypervalent Iodine(III) Sulfonate, and o-phenylenediamines. Significant rate enhancements and improved yields have been observed.
- Lin, Pei-Ying,Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Chen, Ling-Ching
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experimental part
p. 683 - 687
(2010/08/13)
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- Biomimetic synthesis of quinoxalines in water
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Various quinoxalines have been synthesized for the first time in the presence of β-cyclodextrin in water. Biomimetic catalysis of β-cyclodextrin is explained by using 1H NMR spectroscopy.
- Madhav,Narayana Murthy,Prakash Reddy,Rama Rao,Nageswar
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experimental part
p. 6025 - 6028
(2010/03/01)
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- A recyclable copper catalysis in quinoxaline synthesis from α-hydroxyketones and o-phenylenediamines
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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
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experimental part
p. 3215 - 3217
(2010/01/06)
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- Heterocyclizations via TosMIC-based multicomponent reactions: A new approach to one-pot facile synthesis of substituted quinoxaline derivatives
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A novel multicomponent reaction involving o-phenylenediamines, aldehydes and p-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of a base leading to the formation of quinoxalines in very good yields is described. Georg Thieme Verlag Stuttgart.
- Neochoritis, Constantinos,Stephanidou-Stephanatou, Julia,Tsoleridis, Constantinos A.
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scheme or table
p. 302 - 305
(2009/06/23)
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- A cyclic vicinal bis(tetraketone) and structural investigations of formoins
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Investigations of simple formoins such as 2,5-bis(1,1-dimethyl-2- phenylethyl)-2,4-dihydroxyfuran-3(2H)-one (17), benzoylformoin (18), p-toluoylformoin (19), pivaloylformoin (20), and the 2,4-dihydroxy-2,5- bis(heterocycl-2-yl)furan-3-ones 21-23 (heterocycle = furan, thiophene, selenophene) by NMR spectroscopy in DMSO showed the dihydroxyfuranone skeleton and not an enediol structure. The formoin 17 was oxidized to the corresponding tetraketone 10, The intermolecular double benzoin condensation of 1,4-bis(2,2-dimethyl-3,4-dioxobutyl)benzene (27) affords, in low yield, the bis(formoin) 29, and this could be oxidized to provide 2,2,2′,2′,7, 7,7′,7′-octamethyl[8.8]paracyclophan-3,3′,4,4′5, 5′6,6′-octaone (9). The molecular structures of 17 and 29, the monohydrate of 10 (30), and also the dihydrate of 9 (31) are reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Peter, Matthias,Gleiter, Rolf,Rominger, Frank,Oeser, Thomas
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p. 3212 - 3220
(2007/10/03)
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- Iron-catalyzed cross-coupling reactions
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Simple iron salts such as FeCln, Fe(acac)n (n = 2,3) or the salen complex 4 turned out to be highly efficient, cheap, toxicologically benign, and environmentally friendly precatalysts for a host of cross-coupling reactions of alkyl o
- Fuerstner, Alois,Leitner, Andreas,Mendez, Maria,Krause, Helga
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p. 13856 - 13863
(2007/10/03)
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- Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins
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A series of 3-indoleacrylonitrile tyrphostins, 2-chloro-3- phenylquinolines, and 3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF- RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol group in tyrphostins active against EGFR kinase inhibition at different sites. The inhibitors showed selectivity for PDGF and were not active against EGF receptor and HER-2/c-ErbB-2 receptor.
- Gazit, Aviv,App, Harald,McMahon, Gerald,Chen, Jefferey,Levitzki, Alexander,Bohmer, Frank D.
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p. 2170 - 2177
(2007/10/03)
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- Oxidation of diazo compounds by dimethyl dioxirane: An extremely mild and efficient method for the preparation of labile α-oxo-aldehydes
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A novel method for the preparation of α-oxo-aldehydes by dimethyl dioxirane oxidation of α-diazoketones is described. The procedure is particularly useful when the desired compound cannot be purified by chromatography or distillation: the by-products (ace
- Ihmels,Maggini,Prato,Scorrano
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p. 6215 - 6218
(2007/10/02)
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- Protophane und Polyaromaten, XXV. Ringverknuepfende Synthese von Thienyl- und Benzthienylchinoxalinen
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2-(2-Thienyl)- (1a), 2-(3-thienyl)- (2a), and 2,3-di(2-thienyl)quinoxaline (1b), hitherto only accessible by multi-stage ring-forming syntheses, and similar thiophene- and benzothiophene-quinoxaline combinations have been prepared by easily practicable ring-connecting syntheses.Some of the products are favourable starting materials for the synthesis of open-chain polyaromatics and cyclopolyaromatics.
- Kauffmann, Thomas,Ghanem, Mohammad,Otter, Rolf
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p. 459 - 466
(2007/10/02)
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