57433-51-9Relevant academic research and scientific papers
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
Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions
Bains, Amreen K.,Singh, Vikramjeet,Adhikari, Debashis
, p. 14971 - 14979 (2020/11/30)
Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora of heterocyclic rings. Herein, we report an efficacious, nickel-catalyzed synthesis of two important heterocycles such as quinoline and quinoxaline. The catalyst is molecularly defined, is phosphine-free, and can operate at a mild reaction temperature of 80 °C. Both the heterocycles can be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alcohol/1-phenylethanol and diamine/diol, respectively, in a shorter span of reaction time. This environmentally benign synthetic protocol employing an inexpensive catalyst can rival many other transition-metal systems that have been developed for the fabrication of two putative heterocycles. Mechanistically, the dehydrogenation of secondary alcohol follows clean pseudo-first-order kinetics and exhibits a sizable kinetic isotope effect. Intriguingly, this catalyst provides an example of storing the trapped hydrogen in the ligand backbone, avoiding metal-hydride formation. Easy regeneration of the oxidized form of the catalyst under aerobic/O2 oxidation makes this protocol eco-friendly and easy to handle.
Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives
Che, Tong,Kang, Hua-Jie,Peng, Dongming,Shu, Bing,Song, Jia-Lin,Wang, Xiao-Tong,Xie, Hui,Zhang, Luyong,Zhang, Shang-Shi,Zhong, Mei
, (2020/06/25)
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.
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
, 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.
Application of a reusable Co-based nanocatalyst in alcohol dehydrogenative coupling strategy: Synthesis of quinoxaline and imine scaffolds
Panja, Dibyajyoti,Paul, Bhaskar,Balasubramaniam, Bhuvaneshwari,Gupta, Raju K.,Kundu, Sabuj
, (2020/01/21)
A nitrogen doped carbon supported cobalt catalyzed efficient synthesis of imines and quinoxaline motifs is reported. Co(OAc)2-Phen/Carbon-800 (Co-phen/C-800) showed the superior reactivity compared to other materials prepared at different temperature, in the synthesis of quinoxalines by the coupling between diamines and diols. Moreover, applying the transfer hydrogenation and acceptorless dehydrogenative coupling strategy, imines and quinoxaline derivatives were synthesized from the nitro compounds. The practical applicability of this protocol was demonstrated by the gram-scale synthesis and the reusability of the catalyst upto 8th cycle. Furthermore, several kinetic experiments were carried out to realize the probable mechanism.
Manganese(I)-Catalyzed Sustainable Synthesis of Quinoxaline and Quinazoline Derivatives with the Liberation of Dihydrogen
Mondal, Akash,Sahoo, Manoj Kumar,Subaramanian, Murugan,Balaraman, Ekambaram
, p. 7181 - 7191 (2020/07/21)
Direct synthesis of N-heterocycles via the acceptorless dehydrogenative coupling is very challenging and scarcely reported under 3d transition-metal catalysis. Here, we have developed an efficient Mn(I)-catalyzed sustainable synthesis of various quinoxalines from 1,2-diaminobenzenes and 1,2-diols via the acceptorless dehydrogenative coupling reaction. Further, this strategy was successfully applied for the unprecedented synthesis of quinazolines by the reaction of 2-aminobenzyl alcohol with primary amides. The present protocol provides an atom-economical and sustainable route for the synthesis of various quinoxaline and quinazoline derivatives by employing an earth-abundant manganese salt and simple phosphine-free NNN-tridentate ligand.
An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives
Bhargava, Sangeeta,Soni,Rathore, Deepti
, (2019/08/08)
A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship between the catalytic activity and acidity was discussed. It was also found that among the all ILs, [Bmim]CF3SO3 was the most effective, eco-friendly and less expensive solvent and catalyst for the above etiquette. This method is of significant value due to the eco-friendly nature of ionic liquid and non usage of separate catalyst to drive the reaction forward. The protocol proves to be efficient and environmentally benign in terms of good to excellent yields, low reaction times, simple work-up, ease of recovery, and reusability of ionic liquid for six times.
Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water
Chakrabarti, Kaushik,Maji, Milan,Kundu, Sabuj
supporting information, p. 1999 - 2004 (2019/04/27)
Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies.
Selective synthesis of (1: H-benzo [d] imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine
Zhan, Zhenzhen,Ma, Haojie,Cui, Xinfeng,Jiang, Pengbo,Pu, Jinghong,Zhang, Yixin,Huang, Guosheng
supporting information, p. 5148 - 5152 (2019/06/03)
We have designed a general, inexpensive, and versatile method for the synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and the formation of C-N bonds via an aromatic aldehyde and o-phenylenediamine. In the presence of N,N-dimethylformamide/sulfur, (1H-benzo[d]imidazol-2-yl)(phenyl)methanone was obtained; however, in the absence of sulfur, quinoxaline was obtained in 1,4-dioxane. A wide range of quinoxalines and (1H-benzo[d]imidazol-2-yl)(phenyl)methanones was obtained under mild conditions.
Phosphine free Mn-complex catalysed dehydrogenative C-C and C-heteroatom bond formation: A sustainable approach to synthesize quinoxaline, pyrazine, benzothiazole and quinoline derivatives
Das, Kalicharan,Mondal, Avijit,Srimani, Dipankar
supporting information, p. 10582 - 10585 (2018/09/25)
Herein the first sustainable synthesis of quinoxalines, pyrazines and benzothiazoles catalysed by a phosphine free Mn(i) complex via acceptorless dehydrogenative coupling (ADC) is reported. This method is also applied successfully to synthesize quinolines via the dehydrogenation (removal of H2) and condensation (removal of H2O) reaction between 2-aminobenzyl alcohols and secondary alcohols.
