- Vitamin B1 as a metal-ion-free natural catalyst for sustainable quinoxaline ring condensation under sonochemical conditions
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The role of vitamin B1 as a catalyst is investigated for the quinoxaline ring condensation under various mild reaction conditions. The results revealed that the combination of vitamin B1 and ultrasonic irradiation promotes the reaction more efficiently. The salient features of this environmentally benign method are fast conversions, excellent yields for a wide range of substrates, and the use of a low-cost, readily available, nontoxic, and metal-ion-free natural catalyst. The wide range of turnover frequency values (6-400 h-1) shows that the reaction rate is highly dependent on the nature of the functional groups on the aromatic ring of substrates. Moreover, a plausible mechanism for the catalytic action of vitamin B1 has been introduced.
- Aghapoor, Kioumars,Mohsenzadeh, Farshid,Talebian, Shiva,Tehrani, Mohammad Jafar,Balavar, Yadollah,Khanalizadeh, Golriz,Darabi, Hossein Reza
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Read Online
- In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
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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
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supporting information
p. 983 - 1002
(2021/02/27)
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- A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives
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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
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p. 2533 - 2543
(2020/05/18)
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- 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
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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
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p. 915 - 929
(2018/03/01)
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- PTSA-catalyzed one-pot synthesis of quinoxalines using DMSO as the oxidant
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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
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p. 1507 - 1518
(2016/09/28)
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- Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst
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In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.
- Shamsi-Sani, Mahnaz,Shirini, Farhad,Abedini, Masoumeh,Seddighi, Mohadeseh
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p. 1091 - 1099
(2016/04/26)
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- 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
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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
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p. 409 - 422
(2015/10/28)
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- A zirconium Schiff base complex immobilized on starch-coated maghemite nanoparticles catalyzes heterogeneous condensation of 1,2-diamines with 1,2-dicarbonyl compounds
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A magnetically separable zirconium Schiff base nanocatalyst was synthesized under ultrasonic agitation. TEM images revealed a uniform spherical particle shape with average size of 10-14 nm for the as-prepared catalyst. The catalytic performance of ZrOL2@SMNP in the heterogeneous condensation of various 1,2-diamines and 1,2-dicarbonyls for the synthesis of heterocyclic compounds in ethanol has been explored.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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p. 205 - 211
(2016/02/20)
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- Visible-light-induced C=C bond cleavage of enaminones for the synthesis of 1,2-diketones and quinoxalines in sustainable medium
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The C=C double bond cleavage of enaminones has been realized under ambient conditions through visible-light catalysis in the presence of Rose Bengal, which leads to the synthesis of a class of 1,2-diketones without using any metal catalyst. In addition, the one-pot synthesis of quinoxalines has also been achieved under identical photocatalytic conditions by making use of the in situ generated 1,2-diketones as intermediates.
- Cao, Shuo,Zhong, Shanshan,Xin, Luoting,Wan, Jie-Ping,Wen, Chengping
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p. 1478 - 1482
(2015/06/24)
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- An efficient iodine-DMSO catalyzed synthesis of quinoxaline derivatives
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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
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p. 1831 - 1837
(2015/03/04)
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- Nano SbCl5.SiO2: An efficient catalyst for the synthesis of quinoxaline derivatives at room temperature under solventless condition
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Nano SbCl5.SiO2 as an eco-friendly and efficient nanocatalyst was applied for quinoxaline derivatives preparation with improved yield. In this protocol, α-diketones and 1,2-diamines were condensed in the presence of nanocatalyst at room temperature under solventless conditions. The method gave good yields of quinoxaline derivatives in short reaction times in comparison with earlier methods. Using nontoxic and inexpensive materials, simple work-up, short reaction times and high yields of the products are the advantages of this method.
- Bamoniri, Abdolhamid,Mirjalili, Bibi Fatemeh,Karbasizadeh, Hassan
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p. 2851 - 2856
(2015/06/02)
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- Yb modified NaY zeolite: A recyclable and efficient catalyst for quinoxaline synthesis
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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
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supporting information
p. 1203 - 1206
(2014/08/18)
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- 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
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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
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p. 676 - 682
(2014/02/14)
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- A green and efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using heteropolyanion-based ionic liquids: As a recyclable solid catalyst
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In this paper, we introduce two nonconventional ionic liquid compounds which are composed of propane sulfonate functionalized organic cations and heteropolyanions as green solid acid catalysts for the highly efficient and green synthesis of 2,3-disubstitutedquinoxaline derivatives. These ionic liquids are in the solid state at room temperature and the synthesis is carried out via the one-pot condensation reaction of various o-phenylenediamine with 1,2-diketone derivatives. Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the one-pot condensation from reaction orthoester with o-aminophenol (synthesis of benzoxazole derivatives) and ophenylenediamine (synthesis of benzimidazole derivatives). All experiments successfully resulted in the desired products. The described novel synthesis method has several advantages of safety, mild condition, high yields, short reaction times, simplicity and easy workup compared to the traditional method of synthesis.
- Vahdat, Seyed Mohammad,Baghery, Saeed
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p. 618 - 627
(2013/09/12)
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- Surfactant micelles as microreactors for the synthesis of quinoxalines in water: Scope and limitations of surfactant catalysis
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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.
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p. 15157 - 15168
(2013/09/02)
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- Zirconium triflate: An efficient catalyst for the synthesis of quinolines and quinoxalines
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An environmentally friendly method is described for the preparation of substituted quinoline and quinoxaline derivatives using Zr(OTf)4 as an efficient catalyst. The method is based on using 1,3-diketones, ketones and 2-aminoaryl ketones under solvent-free conditions and also on using 1,2-diketone, 1,2-diamine in EtOH/H2O at room temperature for quinloine and quinoxaline synthesis, respectively. The advantages in using this method, include its environmental friendliness, simple operating process and good yields.
- Kolvari, Eskandar,Zolfigol, Mohammad Ali,Koukabi, Nadiya,Gilandust, Maryam,Kordi, Abdol-Vahid
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p. 1183 - 1191
(2013/11/06)
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- Thiamine hydrochloride: An efficient catalyst for one-pot synthesis of quinoxaline derivatives at ambient temperature
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Quinoxaline derivatives have been synthesized in high to excellent yields in the presence of thiamine hydrochloride (VB1) as an inexpensive, non-toxic and metal ion free catalyst at ambient temperature.
- Pawar, Omprakash B.,Chavan, Fulchand R.,Suryawanshi, Venkat S.,Shinde, Vishnu S.,Shinde, Narayan D.
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p. 159 - 163
(2013/05/09)
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- Rice husk: A mild, efficient, green and recyclable catalyst for the synthesis of 12-Aryl-8, 9, 10, 12-tetrahydro [a] xanthene-11-ones and quinoxaline derivatives
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Rice husk, as a green and cheap reagent, can be used for the promotion of the synthesis of 12-aryl -8, 9,10,12-tetrahydrobenzo[α] xanthen-11-one derivatives (ATXOs) via three-component reaction of aldehydes, 2-naphthol and 5,5-dimethyl-1,3-cyclohexadione (dimedone) under solvent-free conditions. This catalyst can also be used for the preparation of quinoxaline derivatives in a mixture of H2O and CH3CN at 50 °C. The present methodology offers several advantages such as high yields, simple procedure, low cost, short reaction times, mild reaction conditions and use of a green, cheap and reusable catalyst.
- Shirini, Farhad,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali,Aliakbar, Ali-Reza
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p. 207 - 216
(2013/05/09)
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- Catalytic application of recyclable silica-supported bismuth(III) chloride in the benzo[N,N]-heterocyclic condensation
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Silica-supported bismuth(III) chloride (BiCl3/SiO2) has been successfully employed in the condensation of 1,2-dicarbonyls with a variety of arene-1,2-diamines bearing either electron withdrawing or donating functional groups. The catalyzed reaction proceeded smoothly under ambient temperature in methanol to give the corresponding quinoxaline and pyrido[2,3-b]pyrazine compounds in good to excellent yields. The catalyst exhibited remarkable reusable activity and higher catalytic performance than homogeneous BiCl3. A plausible mechanism for the catalytic action of BiCl3/SiO2 has been introduced. Moreover, the crystal structure of the prepared unsymmetrical benzo[N,N]-heterocycles has been determined by single crystal X-ray diffraction.
- Aghapoor, Kioumars,Mohsenzadeh, Farshid,Shakeri, Atena,Darabi, Hossein Reza,Ghassemzadeh, Mitra,Neumüller, Bernhard
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p. 170 - 178
(2013/10/08)
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- Reusable α-MoO3 nanobelts catalyzes the green and heterogeneous condensation of 1,2-diamines with carbonyl compounds
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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
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p. 2087 - 2095
(2013/10/08)
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- A reusable zirconium(IV) Schiff base complex catalyzes highly efficient synthesis of quinoxalines under mild conditions
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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
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- Sustainable approach to tandem catalysis: Expedient access to quinoxalines and pyrido[2,3-b]pyrazines from α-hydroxyketones via microwave-induced [(NH4)6Mo7O24·4H 2O - PEG 300] polar paste catalyst system
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[(NH4)6Mo7O24·4H 2O-PEG 300] is introduced as a polar paste catalyst system for tandem synthesis of quinoxalines and pyrido[2,3-b]pyrazines under open-vessel focused microwave irradiation. Low conversions were obtained when catalyst or PEG was used individually. Accordingly, a convenient combination of catalyst and PEG mostly led to quantitative yield of products within 15 min microwave irradiation with good turnover frequency values (11-20 h-1) taking a tandem process into consideration. The salient features of this environmentally benign method are fast conversions, high product selectivity and the use of a low-cost, readily available, nontoxic, catalyst and medium.
- Aghapoor, Kioumars,Mohsenzadeh, Farshid,Mohebi Morad, Mina,Darabi, Hossein Reza
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p. 764 - 767
(2012/10/29)
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- Polyaniline/SiO2 nanocomposite catalyzed efficient synthesis of quinoxaline derivatives at room temperature
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Polyaniline/SiO2 nanocomposite material has been synthesized by using chemical oxidative method. Prepared catalytic material was characterized by means of transmission electron microscopy (TEM), thermal analysis (TG-DTA), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS) and Fourier transform infrared spectroscopy (FT-IR). Solvent stability for the catalyst has been screened using UV-Visible spectroscopy. Polyaniline/SiO2 catalyzed route has found to be an efficient and rapid protocol for the synthesis of quinoxaline derivatives by cyclocondensation of 1,2-diketones and o-phenylenediamines at room temperature. This protocol has several advantages such as high yield, good thermal stability, simple work up procedure, non-toxic, clean, and easy recovery and reusability of the catalytic system.
- Yelwande, Ajeet A.,Navgire, Madhukar E.,Arbad, Balasaheb R.,Lande, MacHhindra K.
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experimental part
p. 995 - 1000
(2012/10/08)
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- Polystyrene-supported AlCl3 as a highly active and reusable heterogeneous lewis acid catalyst for the one-pot synthesis of quinoxalines
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A new and environmentally benign protocol for the synthesis of quinoxaline derivatives through the condensation reactions of 1,2-diketones and 1,2-phenylenediamines using cross-linked polystyrene-supported aluminum chloride (PS/AlCl3) as a highly active and reusable heterogeneous Lewis acid catalyst is described. This polymeric catalyst is stable and can be easily recovered and reused without appreciable change in its efficiency. Copyright
- Rahmatpour, Ali
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p. 472 - 477
(2012/10/29)
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- Fe/Al-MCM-41: An efficient and reusable catalyst for the synthesis of quinoxaline derivatives
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Fe/Al-MCM-41was found to be an effective catalyst for the synthesis of quinoxaline derivatives from the condensation of the 1,2-diamines and 1,2-dicarbonyl compounds in good yields. The catalyst is recyclable and reusable.
- Heravi, Majid M.,Hosseini, Mariam,Oskooie, Hossein A.,Baghernejad, Bita
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experimental part
p. 235 - 239
(2011/06/26)
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- Nano-BF3·SiO2: A reusable and eco-friendly catalyst for synthesis of quinoxalines
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2,3-Disubstituted quinoxalines were synthesized via condensation of α-diketones and 1,2-phenylenediamines. Nano-BF3·SiO 2 as a "green" and reusable solid acid was used as the catalyst for the synthesis of quinoxalines. The reaction was carried out at room temperature under sonication with high to excellent yields.
- Mirjalili,Bamoniri,Akbari
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experimental part
p. 487 - 491
(2012/01/13)
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- Nano-TiO2: An eco-friendly alternative for the synthesis of quinoxalines
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Nano-TiO2 as an eco-friendly and efficient nanocatalyst was applied for quinoxaline preparation with improved yield. In this protocol, diketones and 1,2-diamines were condensed in the presence of catalyst at room temperature.
- Mirjalili, Bi Bi Fatemeh,Akbari, Ali
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experimental part
p. 753 - 756
(2012/01/05)
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- Niobium pentachloride as a highly efficient catalyst for the synthesis of quinoxaline derivatives
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Niobium pentachloride is found to be an efficient catalyst for the synthesis of quinoxaline derivatives via the condensation of aromatic 1,2-dicarbonyl compounds (or unsymmetrical 1,2-diketones or α-hydroxy ketones) with 1,2-diamines. All the reactions were performed at room temperature while using acetonitrile as solvent. The present methodology offers several advantages such as excellent yields, short reaction time and environmentally benign milder reaction conditions.
- Kidwai, Mazaahir,Mishra, Neeraj Kumar,Bhatnagar, Divya,Jahan, Anwar
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experimental part
p. 5051 - 5054
(2012/07/03)
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- Efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using glycerol as green solvent
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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.
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experimental part
p. 5697 - 5701
(2011/11/04)
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- Heterogeneous SnCl2/SiO2 versus homogeneous SnCl 2 acid catalysis in the benzo[N,N]-heterocyclic condensation
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The scope of homogeneous Lewis acid-catalyzed benzo[N,N]-heterocyclic condensation was expanded to include the use of various metal salts not reported in the literature and SnCl2·2H2O was finally selected. Among various solid supports activated with SnCl2, heterogeneous SnCl2/SiO2 proved to be the most effective and significantly higher conversions were achieved compared to SnCl 2·2H2O itself. The results of TG-DTA and BET indicated that dispersed SnCl2 coordinates with surface hydroxyl groups of silica leading to formation of stable Lewis acid sites. Low catalyst loading, operational simplicity, practicability and applicability to various substrates render this eco-friendly approach as an interesting alternative to previously applied procedures.
- Darabi, Hossein Reza,Aghapoor, Kioumars,Mohsenzadeh, Farshid,Jalali, Mohammad Reza,Talebian, Shiva,Ebadi-Nia, Leila,Khatamifar, Ehsan,Aghaee, Ali
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experimental part
p. 213 - 218
(2011/11/06)
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- Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions
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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
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experimental part
p. 48 - 51
(2011/12/16)
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- Synthesis and evaluation of quinoxaline derivatives as potential influenza NS1A protein inhibitors
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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.
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supporting information; experimental part
p. 3007 - 3011
(2011/06/24)
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- Zirconium(IV) chloride as versatile catalyst for the expeditious synthesis of quinoxalines and pyrido[2,3-b]pyrazines under ambient conditions
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Among the various transition metal chlorides, zirconium(IV) chloride was found to be an efficient catalyst for the rapid synthesis of a wide range of 2,3-dialkyl- and 2,3-diaryl-quinoxaline and pyrido[2,3-b]pyrazine derivatives in excellent yields at room temperature. The remarkable features of this catalytic process are the mild reaction conditions, quantitative yields, short reaction times, high conversions, tolerability of various functional groups, clean reaction profiles, and operational simplicity. Graphical Abstract: Among the various transition metal chlorides, zirconium(IV) chloride was found to be an efficient catalyst for the rapid synthesis of a wide range of 2,3-dialkyl- and 2,3-diaryl-quinoxaline and pyrido[2,3-b]pyrazine derivatives in excellent yields at room temperature. The remarkable features of this catalytic process are the mild reaction conditions, quantitative yields, short reaction times, high conversions, tolerability of various functional groups, clean reaction profiles, and operational simplicity.
- Aghapoor, Kioumars,Darabi, Hossein Reza,Mohsenzadeh, Farshid,Balavar, Yadollah,Daneshyar, Hesam
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experimental part
p. 49 - 53
(2011/12/14)
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- ZnO-beta zeolite mediated simple and efficient method for the one-pot synthesis of quinoxaline derivatives at room temperature
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A rapid and an efficient one-pot method for the synthesis of quinoxalines catalysed by ZnO-beta zeolite at room temperature is described. This environmentally benign method provides several advantages over methods that are currently employed such as a simple work-up, mild reaction conditions, good to excellent yields, and a process to recover and reuse the catalyst for several cycles with consistent activity. Versita Warsaw and Springer-Verlag Wien 2010.
- Katkar, Santosh S.,Mohite, Pravinkumar H.,Gadekar, Lakshman S.,Arbad, Balasaheb R.,Lande, Machhindra K.
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experimental part
p. 320 - 325
(2011/10/18)
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- Zirconium tetrakis(dodecyl sulfate) [Zr(DS)4] as an efficient lewis acid-surfactant combined catalyst for the synthesis of quinoxaline derivatives in aqueous media
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Zirconium tetrakis(dodecyl sulfate) [Zr(DS)4] efficiently catalyzes the synthesis of quinoxaline derivatives via the condensation of 1,2-diamines with 1,2-diketones in H2O as a green media at room temperature. Using this method, the title compounds are produced in good to excellent yields and relatively short reaction times. Copyright Taylor & Francis Group, LLC.
- Hasaninejad, Alireza,Zare, Abdolkarim,Zolfigol, Mohammad Ali,Shekouhy, Mohsen
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experimental part
p. 569 - 579
(2009/09/05)
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- MnCl2-promoted synthesis of quinoxaline derivatives at room temperature
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MnCl2 efficiently catalyzes the condensation of o-phenylenediamine derivatives with 1,2-diketones at room temperature to afford the corresponding quinoxaline derivatives in high yields.
- Heravi, Majid M.,Bakhtiari, Khadijeh,Oskooie, Hossein A.,Taheri, Shima
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p. 218 - 220
(2008/09/18)
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- Wells-Dawson type heteropolyacid catalyzed synthesis of quinoxaline derivatives at room temperature
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Wells-Dawson heteropolyacid (H6P2W18O 62 ? 24H2O) was used as an effective catalyst for the synthesis of biologically active quinoxaline derivatives from the condensation of o-phenylenediamines with 1,2-dicarbonyl compounds at room temperature in excellent yields. Springer-Verlag 2007.
- Heravi, Majid M.,Bakhtiari, Khadijeh,Bamoharram, Fatemeh F.,Tehrani, Maryam H.
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p. 465 - 467
(2008/02/02)
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- An efficient and facile synthesis of quinoxaline derivatives catalyzed by KHSO4 at room temperature
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A facile synthesis of quinoxaline derivatives catalyzed by KHSO4 in very high yields at room temperature is reported.
- Oskooie, Hossein A.,Heravi, Majid M.,Bakhtiari, Khadijeh,Taheri, Shima
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p. 875 - 877
(2008/02/11)
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