- In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
-
Substituted quinoxaline derivatives are traditionally synthesized by co-condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o-phenylenediamine and 1,2-diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo-condensation reaction followed by obtaining the aforesaid nitrogen-containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.
- Tamuli, Kashyap J.,Nath, Shyamalendu,Bordoloi, Manobjyoti
-
supporting information
p. 983 - 1002
(2021/02/27)
-
- An efficient and green procedure for the synthesis of quinoxaline derivatives using 3,5-bis(Trifluoromethyl)phenylammonium triflate (bfpat) organocatalyst
-
The application of 3,5-bis(trifluoromethyl)phenylammonium triflate (BFPAT) as a conven-ient new organocatalyst for the synthesis of quinoxaline derivatives is described. In the presence of BFPAT, one-pot synthesis of a wide variety of quinoxaline derivati
- Alipour, Mandana,Hossaini, Zinatossadat,Khaksar, Samad,Rostami-Charati, Faramarz
-
p. 183 - 186
(2021/03/19)
-
- Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives
-
Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to 90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.
- Amaya-García, Fabián,Caldera, Michael,Koren, Anna,Kubicek, Stefan,Menche, J?rg,Unterlass, Miriam M.
-
p. 1853 - 1863
(2021/04/02)
-
- NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy
-
A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.
- Wang, Yan-Bing,Shi, Linlin,Zhang, Xiaojie,Fu, Lian-Rong,Hu, Weinan,Zhang, Wenjing,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
-
p. 947 - 958
(2021/01/14)
-
- Ruthenium?p-cymene complexes with acylthiourea, and its heterogenized form on graphene oxide act as catalysts for the synthesis of quinoxaline derivatives
-
Synthesis of a series of half-sandwich Ru(II) complexes (1-5) containing acylthiourea ligand is reported herein. All the Ru(II) complexes were well characterized by analytical and spectroscopic (UV-Vis, FT-IR, NMR and mass spectrometry) methods. Molecular structures of two (2 and 3) of the complexes were confirmed by single crystal X-ray diffraction, and the complexes adopted pseudo-octahedral geometry around Ru. Catalytic ability of the Ru complexes was evaluated in the synthesis of quinoxaline compounds from various 2-nitroaniline and hydroxy ketone derivatives via transfer hydrogenation approach. Active homogeneous catalyst was heterogenized by supporting it on graphene oxide, and the heterogeneous equivalent was characterized by Raman, XPS, TEM, SEM and ICP-OES techniques. Activity of the heterogeneous catalyst was tested, and it can be reused up to five cycles without any loss in activity.
- Bhuvanesh, Nattamai,Gopiraman, Mayakrishnan,Karvembu, Ramasamy,Sindhuja, Dharmalingam,Vasanthakumar, Punitharaj
-
-
- [BBSA-DBN][HSO4]: a novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines
-
Abstract: A novel –SO3H difunctionalized Bronsted acidic ionic liquid (BAIL) 1, 5-bis (butanesulphonic acid)-diazobicyclo [4,3,0] non-5-enium hydrogen sulphate [BBSA-DBN][HSO4] is introduced for efficient synthesis of quinoxalines vi
- Patil, Megha U.,Shinde, Sachinkumar K.,Patil, Sandip P.,Patil, Suresh S.
-
p. 4923 - 4938
(2020/08/24)
-
- Organocatalytic combinatorial synthesis of quinazoline, quinoxaline and bis(indolyl)methanes
-
Aims and Objective: An efficient and practical procedure for the synthesis of heterocyclic compounds such as quinazolines, quinoxalines and bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. Materials and Methods: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Result: Various products were obtained in good to excellent yields under reaction conditions Conclusion: The BFPHP organocatalyst demonstrates a novel class of non-asymmetric organocatalysts, which has gained much attention in green chemistry.
- Badri, Rashid,Khaksar, Samad,Malamiri, Fatemeh,Tahanpesar, Elham
-
-
- Dowex 50W: Mild efficient reusable heterogeneous catalyst for synthesis of quinoxaline derivatives in aqueous medium
-
An efficient, simple and eco-friendly procedure is reported in presence of heterogeneous Dowex 50W catalyst in aqueous medium under refluxing condition to produce quinoxaline derivatives. Catalyst has participated in condensation reaction between 1,2-diamines and various aromatic 1,2-diketones smoothly with excellent yield of the products in short reaction times. Dowex 50W was used more than five times in this reaction separately and showed an excellent recyclability throughout the reaction.(figure presented).
- Datta, Arup,Halder, Samiran
-
p. 1218 - 1224
(2021/02/09)
-
- A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives
-
In this study, a novel acid-functionalized magnetic nanoparticles with high loaded multifunctional acidic groups was fabricated by anchoring water-soluble 5-sulfosalicylic acid onto the surface silica-modified Fe3O4. The magnetically recyclable Fe3O4@SiO2@5-SA (20?mg) showed excellent reactivity for greener synthesis of tetrahydrobenzo[b]pyrans via a three-component reaction of different aromatic aldehydes, malononitrile and dimedone in good to excellent yields (70–95percent) in pure water at short reaction times (40–150?min). The method shows eco-friendly synthesis of quinoxaline derivatives from direct condensation of substituted 1,2-diamine with various 1,2-dicarbonyl in ethanol at room temperature to afford the desired quinoxalines with good to excellent yields (60–97percent) at shorter reaction times (120–240?min). The morphology and magnetic properties of MNPs were studied with scanning electron microscopy, X-ray powder diffraction, Fourier translation infrared spectroscopy, vibrating sample magnetometer and thermogravimetric. The results showed that the Fe3O4@SiO2@5-SA catalyst is completely recoverable by an external magnet and retained catalytic activity after five recycles.
- Saboury, Farzaneh,Azizi, Najmedin,Mirjafari, Zohreh,Mahmoudi Hashemi, Mohammad
-
p. 2533 - 2543
(2020/05/18)
-
- Transition Metal-Free Heteroarylation of Quinoxaline: Construction of Heteroaryl-Fused Phenazines by Oxidative Coupling
-
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
-
p. 15502 - 15513
(2020/11/30)
-
- Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One-Pot Synthesis of Imines and Quinoxalines
-
Three copper(I) complexes, [CuCl(L)(PPh3)2] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh3)2Cu(μ-Cl)2Cu(PPh3)] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1H NMR, 13C NMR and 31P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to catalyse the one-pot synthesis of imines and quinoxalines. Heterogenized catalyst (4) was prepared by reacting more active complex 3 with polystyrene supported triphenylphosphane, and characterized by elemental analyses, and DRS-UV, FT-IR, ICP-OES, and solid-state NMR techniques. Catalytic activity of the complexes (3 and 4) was tested in the formation of imines from alcohols and amines, and quinoxalines from hydroxy ketones and diamines. Heterogeneity and reusability of catalyst 4 were evaluated, and the catalyst can be reused for four runs without any loss in activity.
- Sindhuja, Dharmalingam,Vasanthakumar, Punitharaj,Bhuvanesh, Nattamai,Karvembu, Ramasamy
-
p. 3588 - 3596
(2019/08/20)
-
- Synthesis of a polymer-capped palladium nanoparticles and its application as a reusable catalyst in oxidative coupling reaction of α-hydroxyketones and 1,2-diamines for preparation of pyrazines and quinoxalines
-
A novel method for the synthesis of pyrazines and quinoxalines has been developed using α-hydroxyketones and 1,2-diamines in the presence of cross-linked poly(4-vinylpyridine)-stabilized Pd(0) nanoparticles, [P4-VP]-PdNPs. The catalyst was easily prepared and characterized using various techniques such as FT-IR and UV–Vis spectroscopy, AAS, TEM, FESEM, EDX analysis and XRD. The results confirm a good dispersion of palladium nanoparticles on the polymer support. The catalyst displayed good catalytic activity when applied to the synthesis of quinoxalines via condensation of α-hydroxyketones with 1,2-diamines. A few pyrazine derivatives and various quinoxalines are prepared via coupling reaction of α-hydroxyketones and 1,2-diamines in high–excellent yields (81–99%) with short reaction times. The quinoxalines products were characterized by FT-IR, 1H and 13C NMR spectroscopy, and the physical properties were compared to the literature values of known compounds. The advantages of the present method over conventional classical methods are rapid and very simple work-up, and the catalyst is reusable many times without a significant loss in its activity.
- Zarchi, Mohammad Ali Karimi,Abadi, Seyed Shahab Addin Darbandizadeh Mohammad
-
p. 915 - 929
(2018/03/01)
-
- 2-Iodo benzoic acid: An unconventional precursor for the one pot multi-component synthesis of quinoxaline using organo Cu (II) catalyst
-
This is the first reported, unconventional, efficient strategy for the synthesis of quinoxaline from 2 to iodo benzoic acid and sodium azide in presence of organo Cu (II) catalyst. Herein, a very simple, versatile one pot multi-component protocol for the synthesis of biologically active compound, quinoxaline has been described via Schmidt reaction and the nucleophilic substitution reaction. The isolated compounds were characterized by 1H NMR, 13C NMR. Our reported organo catalyst was characterized by single crystal XRD, SEM.
- Saha, Bittu,Mitra, Bijeta,Brahmin, Dhiraj,Sinha, Biswajit,Ghosh, Pranab
-
supporting information
p. 3657 - 3663
(2018/09/12)
-
- CO2-assisted synthesis of non-symmetric α-diketones directly from aldehydes: Via C-C bond formation
-
CO2-assisted various symmetric and non-symmetric α-diketones have been synthesized directly from the corresponding aldehydes using transition metal-free catalysts. This method can even be applied to synthesize pharmaceuticals directly from aldehydes. The crucial role of CO2 has been investigated in detail and the mechanism is proposed on the basis of experiments and DFT calculations.
- Hirapara, Pradipbhai,Riemer, Daniel,Hazra, Nabanita,Gajera, Jignesh,Finger, Markus,Das, Shoubhik
-
p. 5356 - 5360
(2017/11/22)
-
- ZnO-loaded mesoporous silica (KIT-6) as an efficient solid catalyst for production of various substituted quinoxalines
-
Conventional homogeneous and microporous heterogeneous catalysts for quinoxalines production from diamines and diketones usually suffer from difficult separation or harsh reaction conditions. Here, we demonstrate the production of various substituted quin
- Hamid, Oveisi,Chari, M. Adharvana,Van Nguyen, Chi,Chen, Jeffrey E.,Alshehri, Saad M.,Yanmaz, Ekrem,Hossain, Shahriar A.,Yamauchi, Yusuke,Wu, Kevin C.-W.
-
p. 111 - 115
(2016/12/30)
-
- PTSA-catalyzed one-pot synthesis of quinoxalines using DMSO as the oxidant
-
An efficient p-toluene sulfonic acid–catalyzed, one-pot, two-step oxidative system for cyclization of o-diaminobenzene with 1,2-diaryl-2-hydroxyethanone to quinoxalines was described. A nontoxic, readily available oxidant, dimethylsulfoxide (DMSO), was applied in this process. A broad range of substrates was applied to this method, and target compounds were obtained with good yields.
- Zhang, Zeyuan,Xie, Caixia,Feng, Lei,Ma, Chen
-
p. 1507 - 1518
(2016/09/28)
-
- Fe3O4@SiO2-imid-PMAn magnetic porous nanosphere as recyclable catalyst for the green synthesis of quinoxaline derivatives at room temperature and study of their antifungal activities
-
An efficient, simple, and green procedure for the synthesis of quinoxaline derivatives catalyzed by Fe3O4@SiO2-imid-PMAn nanoparticles at room temperature is described. This environmentally benign method provides several advantages such as mild reaction conditions, good to excellent yields, short reaction times, simple work-up and catalyst stability, easy preparation, heterogeneous nature and easy separation of the catalyst. Also, nanocatalyst can be easily recovered by a magnetic field and reused for the next reactions for at least 6 times without distinct deterioration in catalytic activity. SEM, BET, DLS and leaching of catalyst after each reaction cycle were investigated. Furthermore, antifungal activity of various derivatives against three phytopathogenic fungi (Alternaria alternata, Pyricularia oryzae, and Alternaria brassicae) was investigated.
- Javidi, Jaber,Esmaeilpour, Mohsen
-
p. 409 - 422
(2015/10/28)
-
- N-heterocycles as corrosion inhibitors for mild steel in acid medium
-
The corrosion behavior of mild steel in 1 M H2SO4 was studied using 2,3-diphenylpyrazine (DP), 2,3-di(furan-2-yl)pyrazine (FP) and 2,3-di(furan-2-yl)quinoxaline (FQ) as inhibitors using weight loss, potentiodynamic polarization and electrochemical impedance spectroscopy (EIS) studies. Scanning electron microscopy (SEM) and atomic force microscopy (AFM) methods were utilized for surface characterization. The results showed that the three inhibitors possess excellent inhibition effect toward mild steel corrosion. The inhibitor molecules are adsorbed on the mild steel surface, blocking the reactive sites available for acid attack. Adsorption of the inhibitor was found to obey Langmuir isotherm. Electronic structure calculations were used to study the inhibition efficiency of the inhibitor molecules on Fe (100) surface. The calculated results are in agreement with the experimental findings.
- Saranya, Jagadeesan,Sowmiya, Murugaiyan,Sounthari, Palanisamy,Parameswari, Kandhasamy,Chitra, Subramanian,Senthilkumar, Kittusamy
-
-
- An efficient iodine-DMSO catalyzed synthesis of quinoxaline derivatives
-
An efficient iodine-DMSO catalyzed system for the synthesis of quinoxaline derivatives was developed. The construction of this quinoxaline system went through a one-pot oxidation/cyclization process. The reaction afforded a variety of products in good to excellent yields. This methodology has potential applications in the synthesis of biologically and medicinally relevant compounds.
- Xie, Caixia,Zhang, Zeyuan,Yang, Bingchuan,Song, Gaolei,Gao, He,Wen, Leilin,Ma, Chen
-
p. 1831 - 1837
(2015/03/04)
-
- Graphene oxide (GO) or reduced graphene oxide (rGO): Efficient catalysts for one-pot metal-free synthesis of quinoxalines from 2-nitroaniline
-
A straightforward one-pot preparation of library of quinoxalines from 2-nitroanilines under entirely metal-free conditions is described. Initial reduction of nitroaniline with hydrazine hydrate is efficiently catalyzed by graphene oxide (GO) or reduced graphene oxide (rGO), and further one-pot tandem reactions with 1,2-dicarbonyl compounds or with α-hydroxy ketones afford quinoxalines in excellent yields. The catalyst is recovered, characterized, and found to be recyclable for consecutive four runs examined with appreciable conversions.
- Roy, Babli,Ghosh, Sujit,Ghosh, Pranab,Basu, Basudeb
-
supporting information
p. 6762 - 6767
(2016/01/30)
-
- Protic ionic liquids: A lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans
-
Protic ionic liquids (PILs), which are easily produced through the combination of a Bronsted acid and Bronsted base, such as [Mim]Ac and 1,4-diazabicyclo[ 2.2.2]octane (DABCO):AcOH:H2O (1:1:3), were found to be lucid, tunable tool for synthesis
- Mulik,Chandam,Patil,Patil,Mulik,Salunkhe,Deshmukh
-
p. 10085 - 10096
(2016/01/12)
-
- L-Proline mediated synthesis of quinoxalines; Evaluation of cytotoxic and antimicrobial activity
-
A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employing l-proline as a catalyst in water. To the best of our knowledge this transformation is achieved for the first time using an organic catalyst. A small library of quinoxaline-sulphonamide conjugates have been synthesized using this protocol. The newly synthesized conjugates have been tested for their cytotoxicity and antimicrobial activity against several bacterial strains including one fungal strain. The majority of the compounds have exhibited significant cytotoxicity as well as antimicrobial activity. Compounds 5a, 5b and 5d were found to be promising with respect to both cytotoxicity and antimicrobial activity. This journal is
- Kamal, Ahmed,Babu, Korrapati Suresh,Faazil, Shaikh,Hussaini, S. M. Ali,Shaik, Anver Basha
-
p. 46369 - 46377
(2015/02/19)
-
- Yb modified NaY zeolite: A recyclable and efficient catalyst for quinoxaline synthesis
-
In this study, Yb immobilized NaY zeolite catalyst (Yb/NaY) was obtained by a hydrothermal method and characterized by XRD, BET, FT-IR, ICP-AES, and NH3-TPD. The catalyst displayed good catalytic activity when applied to the synthesis of quinoxalines via condensation of α-hydroxyketones with 1,2-diamines, and could be reused several times without any loss of catalytic activity.
- Fan, Li-Yan,Wei, Lin,Hua, Wen-Jun,Li, Xiang-Xiong
-
supporting information
p. 1203 - 1206
(2014/08/18)
-
- Star-shaped Keggin-type heteropolytungstate nanostructure as a new catalyst for the preparation of quinoxaline derivatives
-
In this work, we report the novel successful preparation of the Keggin-type Cs(CTA)2PW12O40 (CTA = cetyltrimethylammonium cation) nanostructure by a microemulsion method. The microemulsion system included the cationic surfactant CTAB, 1-butanol as co-surfactant, isooctane as oil phase, and an aqueous solution containing CsNO3. The Cs(CTA)2PW12O40 nanostructure was formed by the addition of an aqueous solution of phosphotungstic acid to the microemulsion solution. Characterization of the resultant nanostructure was done using FT-IR spectroscopy, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray analysis, and CHN elemental analysis. The product was found to be a star-shaped nanostructure composed of some nanorods whose diameter and length are about 100 nm and 500 nm, respectively. The prepared nanostructure was used as a recoverable catalyst for the synthesis of quinoxaline derivatives by the condensation of 1,2-diamines with 1,2-dicarbonyl compounds, which afforded the products in good to high yields in short reaction times.
- Masteri-Farahani, Majid,Ghorbani, Melika,Ezabadi, Ali,Farrokhinia, Niki,Ghaemmaghami, Atekeh-Sadat
-
p. 1136 - 1143
(2015/02/05)
-
- Pentafluorophenylammonium triflate: A highly efficient catalyst for the synthesis of quinoxaline derivatives in water
-
A simple, inexpensive, environmentally friendly and efficient route for the rapid and efficient synthesis of quinoxaline derivatives using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. Various quinoxaline derivatives were synthesi
- Khaksar, Samad,Radpeyma, Hanieh
-
p. 1023 - 1027
(2014/12/10)
-
- A highly efficient procedure for the synthesis of quinoxaline derivatives using polyvinylpolypyrrolidone supported triflic acid catalyst (PVPP·OTf)
-
A polyvinylpolypyrrolidone supported triflic acid was shown to be useful as a recyclable heterogeneous catalyst for the rapid and efficient synthesis of quinoxaline derivatives in good-to-excellent yields. The catalyst is easily prepared, air-stable, reus
- Khaksar, Samad,Tajbakhsh, Mahmoud,Gholami, Milad,Rostamnezhad, Fariba
-
p. 1287 - 1290
(2014/10/15)
-
- A novel protocol for selective synthesis of monoclinic zirconia nanoparticles as a heterogeneous catalyst for condensation of 1,2-diamines with 1,2-dicarbonyl compounds
-
ZrO2 nanocatalyst has been obtained successfully using novel and safe agents through a simple and safe sol-gel method (polymerizing-complexing) and characterized by XRD, FT-IR, Raman spectroscopies and transmission electron microscopy (TEM). Raman spectroscopies and XRD results indicated only formation of monoclinic zirconia. TEM images revealed spherical nanoparticles with 20-40 nm diameter range. The spectral and analysis data confirmed the effectiveness of the method for preparation of monoclinic zirconia by preventing grain growth or agglomeration of particles. The nanostructured ZrO2 exhibited high efficiency in catalyzing condensation of various 1,2-diamine and 1,2-dicarbonyl compounds for the synthesis of heterocyclic compounds. The recovery of the title heterogeneous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk one.
- Jafarpour, Maasoumeh,Rezapour, Elham,Ghahramaninezhad, Mahboobe,Rezaeifard, Abdolreza
-
p. 676 - 682
(2014/02/14)
-
- Catalyst-free protocol for the synthesis of quinoxalines and pyrazines in PEG
-
A facile and simple catalyst-free protocol has been developed for the condensation of 1,2-diketones with aromatic 1,2-diamines in polyethylene glycol (PEG), providing quinoxaline derivatives in good yields. The important features of the methodology are broad substrates scope, simple workup, catalyst free, environmentally benign, and no requirement for metal catalysts. It is noteworthy that the cyclization reaction of 1,2-diketones with aliphatic 1,2-diamines is also conducted smoothly to afford pyrazines in good yields under the standard conditions. In addition, PEG could be recovered easily and was reused without evident loss in activity
- Huang, Tie-Qiang,Qu, Wen-Yan,Ding, Jin-Chang,Liu, Miao-Chang,Wu, Hua-Yue,Chen, Jiu-Xi
-
p. 293 - 297
(2013/06/05)
-
- Reusable α-MoO3 nanobelts catalyzes the green and heterogeneous condensation of 1,2-diamines with carbonyl compounds
-
Crystalline nanobelts of α-MoO3 have been obtained successfully using novel and safe agents through a simple and safe sol-gel method (polymerizing-complexing) and characterized by XRD, FT-IR, Raman spectroscopies, high resolution transmission electron microscopy (HRTEM), scanning electron microscopy (SEM) and the temperature programmed desorption (TPD) of ammonia. An orthorhombic lattice system for nano-MoO3 was established. The HRTEM images showed that the nanobelt morphology of α-MoO3 mostly ranged from 20-70 nm in width and 200-400 nm in length. The ammonia TPD profile demonstrated strong acidic sites. The spectral and analysis data confirmed the effectiveness of the method for the preparation of α-MoO3 nanobelts by prevention of grain growth or agglomeration of the particles. The nanostructured MoO3 exhibited a high efficiency in catalyzing the condensation reaction of various 1,2-diamine and carbonyl compounds for synthesis of heterocyclic compounds. The recovery of the title heterogenous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk material.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Ghahramaninezhad, Mahboube,Tabibi, Tooba
-
p. 2087 - 2095
(2013/10/08)
-
- A reusable zirconium(IV) Schiff base complex catalyzes highly efficient synthesis of quinoxalines under mild conditions
-
A zirconium(IV) complex of a bidentate Schiff base (ZrL2Cl 2) has been synthesized by the reaction of (z)-N-benzylidene-2- hydroxypropane-1-amine (HL) and ZrCl4. Spectroscopic data and elemental analyses are consistent with a monomeric complex with a ligand:Zr ratio of 2:1. The catalytic activity of ZrL2Cl2 has been investigated for the efficient synthesis of a wide variety of quinoxaline derivatives under mild conditions. The employment of ethanol as an environmentally benign solvent in this high yield method, along with high turnover numbers and reusability of the catalyst providing ready scalability, makes it appropriate for practical applications.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Haddad, Reza,Gazkar, Somayeh
-
-
- Surfactant micelles as microreactors for the synthesis of quinoxalines in water: Scope and limitations of surfactant catalysis
-
The scope and limitations of surfactants as catalysts for the synthesis of quinoxalines using microreactors made of the surfactants in water has been assessed. The catalytic potential followed the order: non-ionic surfactants > anionic surfactants > Bronsted acid surfactants > cationic surfactants. The non-ionic surfactant, Tween 40, is the most effective catalyst affording excellent yields within a short reaction time at room temperature and is compatible with different variations of the 1,2-diketones and 1,2-diamines. The reaction medium (spent water) containing the catalyst, as well as the catalyst itself (recovered Tween 40) can be reused for five consecutive reactions. The better catalytic efficiency of the surfactant (Tween 40) compared to the various Lewis/Bronsted acids, as well as the surfactant combined Lewis acid, suggests that surfactants, which generate microreactor assemblies at the interface, are better suited as catalytic aids to promote organic reactions in water. The inferior results obtained in organic solvents, which provide a homogeneous reaction mixture compared to those obtained in water, indicate the specific role of water. This has been depicted as a synergistic dual activation through the hydrogen bond mediated formation of supramolecular assemblies involving a water dimer and the reactants. The catalytic assistance of the surfactant could be ascribed to the ability of the surfactant molecule to undergo hydrophobic and hydrogen bond forming interactions with water and the reactants in orienting the reactants at the water interface and encapsulating inside the microreactors to facilitate the cyclocondensation. The Royal Society of Chemistry 2013.
- Kumar, Dinesh,Seth, Kapileswar,Kommi, Damodara N.,Bhagat, Srikant,Chakraborti, Asit K.
-
p. 15157 - 15168
(2013/09/02)
-
- Graphite catalyzed green synthesis of quinoxalines
-
A new simple approach using environmentally benign, cheap, and easily recyclable graphite as a heterogeneous catalyst for the synthesis of quinoxalines is described. A library of pharmacologically interesting diphenylquinoxalines is prepared by the double condensation of substituted benzils, phenanthrene-9,10-dione, and benzoin with aromatic diamines in 71-93% yields at room temperature in ethanol. Aliphatic diamines gave corresponding dihydropyrazines from substituted benzils in 72-92% yields.
- Kadam, Hari K.,Khan, Salman,Kunkalkar, Rupesh A.,Tilve, Santosh G.
-
p. 1003 - 1007
(2013/02/25)
-
- Magnetically separable MnFe2O4 nano-material: An efficient and reusable heterogeneous catalyst for the synthesis of 2-substituted benzimidazoles and the extended synthesis of quinoxalines at room temperature under aerobic conditions
-
A simple and efficient protocol has been developed for the synthesis of biologically relevant 2-substituted benzimidazoles and quinoxalines using magnetically separable manganese ferrite (MnFe2O4) nanopowder for the first time as a reusable heterogeneous catalyst at room temperature under aerobic conditions. MnFe2O4 nanoparticles were prepared by a simple sol-gel method using starch as a bio-polymeric matrix, and characterized by XRD, TEM, EDAX and VSM analyses. The Royal Society of Chemistry 2013.
- Brahmachari, Goutam,Laskar, Sujay,Barik, Puspendu
-
p. 14245 - 14253
(2013/09/02)
-
- N-heterocyclic carbene catalyzed one-pot synthesis of 2,3- diarylquinoxalines
-
A one-pot efficient and facile protocol for the direct synthesis of quinoxaline derivatives via tandem N-heterocyclic carbene (NHC)-catalyzed umpolung of aldehydes/oxidation of the benzoins to benzils/condensation of benzils with benzene-1,2-diamines has been developed. Georg Thieme Verlag Stuttgart New York.
- Lin, Yang,Lei, Xiaoli,Yang, Qin,Yuan, Jiangjun,Ding, Qiuping,Xu, Jingshi,Peng, Yiyuan
-
p. 2699 - 2706
(2012/11/13)
-
- One-pot synthesis of quinoxalines starting from aldehydes under metal-free conditions
-
An efficient and convenient synthesis of quinoxalines from easily available aldehydes was performed as a one-pot procedure in good to excellent yields under metal-free conditions, via sequential benzoin condensation, aerobic formation of benzils and condensation of the latter with 1,2-diaminobenzenes.
- Hu, Zhong-Yuan,Du, Ding,Tang, Wei-Fang,Lu, Tao
-
p. 2262 - 2264
(2012/08/07)
-
- FeCl3 and morpholine as efficient cocatalysts for the one-step synthesis of quinoxalines from α-hydroxyketones and 1,2-diamines
-
One-step conversion including intramolecular hydrogen bond decomposition, aerobic oxidation, and condensation from α-hydroxyketones and 1,2-diamines into quinoxalines is reported using FeCl3 and morpholine as cocatalysts. Taylor & Francis Group, LLC.
- Liu, Peng,Lei, Min,You, Hanyun,Chen, Xubing,Chen, Hu,Ma, Lei,Hu, Lihong
-
experimental part
p. 236 - 245
(2011/11/06)
-
- CaO-catalyzed aerobic oxidation of α-hydroxy ketones: Application to one-pot synthesis of quinoxaline derivatives
-
The aerobic oxidation of α-hydroxy ketones into α-diketones catalyzed by CaO is compared with the same reaction catalyzed by other metal oxides. The catalytic activities of the various metal oxides were proportional to their surface basicities. The direct conversion of α-hydroxy ketones into quinoxalines via CaO-catalyzed aerobic oxidation followed by in situ reaction with 1,2-diaminoaromatics is also achieved. Various types of quinoxalines were synthesized in the presence of the CaO catalyst and molecular oxygen. It was also found that the CaO catalyst was reusable without any loss of its catalytic activity.
- Hara, Takayoshi,Takami, Yukihiro,Ichikuni, Nobuyuki,Shimazu, Shogo
-
experimental part
p. 488 - 490
(2012/08/07)
-
- H3PW12O40/MCM-41 nanoparticles as efficient and reusable solid acid catalyst for the synthesis of quinoxalines
-
The condensation reaction of 1,2-diketones and o-phenylenediamines was investigated in the presence of nano-sized mesoporous silica (MCM-41) supported 12-tungstophosphoric acid (TPA) as solid acid catalyst. Nano-sized MCM-41 was synthesized and the catalysts with different loading amounts of TPA (5-15 wt.%) were prepared and characterized by XRD, FT-IR and SEM techniques. The results confirm good dispersion of TPA on the solid support. The catalyst is reusable many times without loss in its activity.
- Abdollahi-Alibeik, Mohammad,Heidari-Torkabad, Ezzat
-
experimental part
p. 517 - 523
(2012/07/31)
-
- A novel one-pot synthesis of quinoxaline derivatives in fluorinated alcohols
-
Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of quinoxaline derivatives in high yields at room temperature. The solvent (HFIP) can be readily separated from reaction products and recovered in excellent purity for direc
- Khaksar, Samad,Rostamnezhad, Fariba
-
p. 2581 - 2584
(2012/10/29)
-
- Silica sulfuric acid (SSA)/polyethylene glycol (PEG) as a recyclable system for the synthesis of quinoxalines and pyrazines
-
An efficient and facile method has been developed for the condensation of 1,2-diamines with-hydroxyketones in polyethylene glycol (PEG) to quinoxalines and pyrazines with good yields in the presence of silica sulfuric acid (SSA). The important features of the methodology are simple operations, environmentally friendliness, and no requirement for metal catalysts. Additionally, the catalyst system (SSA/PEG) could be recovered easily and reused.
- Huang, Tieqiang,Jiang, Danna,Chen, Jiuxi,Gao, Wenxia,Ding, Jinchang,Wu, Huayue
-
experimental part
p. 3334 - 3343
(2011/09/19)
-
- Eco-friendly synthesis of quinoxaline derivatives by grinding under solvent-free conditions
-
An efficient and facile synthesis of quinoxaline derivatives in excellent isolated yields by the condensation of 1,2-diamines and 1,2-diketones on grinding under solvent-free conditions at ambient temperature has been developed. The important features of this method are that it is reasonably fast, very clean, high yielding, simple workup, and environmentally benign.
- Li, Jun,Jiang, Dan-Na,Chen, Jiu-Xi,Liu, Miao-Chang,Ding, Jin-Chang,Wu, Hua-Yue
-
experimental part
p. 403 - 406
(2011/05/14)
-
- Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions
-
Alumina as a cheap, heterogeneous and reusable catalyst can provide environmentally friendly alternatives for synthesis of quinoxaline derivatives via condensation of 1,2-diamines and 1,2-dicarbonyl compounds under solvent-free conditions. The products could be separated simply from catalyst by filtration and the catalyst could be recycled and reused for several times without noticeably decreasing in catalytic activity.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Danehchin, Maryam
-
experimental part
p. 48 - 51
(2011/12/16)
-
- Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines
-
A variety of biologically important quinoxaline derivatives has been efficiently synthesized in excellent yields under extremely mild conditions using PEG-600 and water. This inexpensive, non-toxic, ecofriendly and readily available system efficiently condensed several aromatic as well as aliphatic 1,2-diketones with aromatic and aliphatic 1,2-diamines to afford the products in excellent yield. Polyethylene glycol (PEG) can be recovered and recycled. Indian Academy of Sciences.
- Chavan, Hemant V.,Adsul, Laxman K.,Bandgar, Babasaheb P.
-
experimental part
p. 477 - 483
(2012/03/26)
-
- A green and efficient synthesis of quinoxaline derivatives catalyzed by 1-n-butyl-3-methylimmidazolium tetrafluoroborate
-
The room temperature ionic liquid 1-n-butyl-3-methylimmidazolium tetrafluoroborate ([bmim]BF4) was used to promote the synthesis of quinoxaline derivatives under grinding condition. The yields were ranged in 86.0-95.1%. It was shown that the proposed method is fast, efficient and environmentally benign.
- Li, Chao,Guo, Tao,Zhou, Xin,Wang, Chun,Ma, Jing-Jun,Hao, Hong-Jing
-
experimental part
p. 455 - 460
(2012/03/11)
-
- Synthesis of quinoxaline derivatives using TiO2 nanoparticles as an efficient and recyclable catalyst
-
TiO2 nanoparticles were synthesized and characterized by SEM and XRD techniques. The TiO2 nanoparticles were employed as a recyclable, inexpensive and efficient catalyst for the synthesis of substituted quinoxalines in high to excellent yields and in relatively short duration.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Salehian, Fatemeh,Biparva, Pourya
-
experimental part
p. 3720 - 3725
(2012/01/11)
-
- Efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using glycerol as green solvent
-
A straightforward, efficient and more sustainable catalyst-free method has been developed for the synthesis of quinoxaline, benzoxazole, and benzimidazole ring system in glycerol to achieve yields that were comparable to or better than, those in conventional media. It is noteworthy that the reaction was exclusively carried out in glycerol-water system, rendering the methodology highly valuable from both environment and economic points of view.
- Bachhav, Harshal M.,Bhagat, Saket B.,Telvekar, Vikas N.
-
experimental part
p. 5697 - 5701
(2011/11/04)
-
- Synthesis and evaluation of quinoxaline derivatives as potential influenza NS1A protein inhibitors
-
A library of quinoxaline derivatives were prepared to target non-structural protein 1 of influenza A (NS1A) as a means to develop anti-influenza drug leads. An in vitro fluorescence polarization assay demonstrated that these compounds disrupted the dsRNA-NS1A interaction to varying extents. Changes of substituent at positions 2, 3 and 6 on the quinoxaline ring led to variance in responses. The most active compounds (35 and 44) had IC50 values in the range of low micromolar concentration without exhibiting significant dsRNA intercalation. Compound 44 was able to inhibit influenza A/Udorn/72 virus growth.
- You, Lei,Cho, Eun Jeong,Leavitt, John,Ma, Li-Chung,Montelione, Gaetano T.,Anslyn, Eric V.,Krug, Robert M.,Ellington, Andrew,Robertus, Jon D.
-
supporting information; experimental part
p. 3007 - 3011
(2011/06/24)
-
- Aqueous-phase aerobic oxidation of alcohols by Ru/C in the presence of cyclodextrin: One-pot biomimetic approach to quinoxaline synthesis
-
The aerobic oxidation of alcohols and synthesis of quinoxalines was developed in a one-pot biomimetic approach using recyclable ruthenium on charcoal and randomly methylated β-cyclodextrin in water under neutral conditions overcoming many of the drawbacks in the earlier methodologies. The catalytic system can be recycled up to five cycles without loss of activity. Georg Thieme Verlag Stuttgart New York.
- Akkilagunta, Vijay Kumar,Reddy, Vutukuri Prakash,Kakulapati, Rama Rao
-
supporting information; experimental part
p. 2571 - 2574
(2010/12/20)
-
- Efficient, ecofriendly, and practical process for the synthesis of quinoxalines catalyzed by amberlyst-15 in aqueous media
-
Amberlyst-15/H2O has been used as an efficient and environmentally friendly catalytic system for the synthesis of quinoxalines. The present methodology offers several advantages, such as excellent yields, short reaction time, and simple workup. Copyright Taylor & Francis Group, LLC.
- Liu, Ju-Yan,Liu, Jing,Wang, Jia-Di,Jiao, De-Quan,Liu, Hai-Wang
-
experimental part
p. 2047 - 2056
(2010/08/13)
-
- Magnetic Fe3O4 nanoparticles as new, efficient, and reusable catalysts for the synthesis of quinoxalines in water
-
A novel, environmentally friendly procedure has been developed for the synthesis of quinoxaline derivatives in the presence of magnetic Fe 3O4 nanoparticles. The reaction between 1,2-diamines and 1,2-dicarbonyl compounds was carried out in water to afford quinoxaline derivatives in high yield. The catalyst can be recovered by the use of an external magnet and reused for five cycles with almost consistent activity. CSIRO 2010.
- Lue, Hong-Yan,Yang, Shu-Hong,Deng, Jia,Zhang, Zhan-Hui
-
experimental part
p. 1290 - 1296
(2011/04/15)
-