- 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.
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p. 1853 - 1863
(2021/04/02)
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- NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy
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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
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p. 947 - 958
(2021/01/14)
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- 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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- Efficient and sustainable Co3O4 nanocages based nickel catalyst: A suitable platform for the synthesis of quinoxaline derivatives
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Engineered nanocages have emerged at the forefront of nanomaterial investigation as they possess tremendous potential to boost key chemical processes owing to their hollow architectures that can help in achieving high reactivity. With an intention to make profitable use of their morphological features guided chemical activity, we developed dispersable Co3O4 nanocages decorated with nickel nanoparticles for accessing a broad spectrum of pharmaceutically and biologically active N-heterocyclic quinoxaline nuclei using α-dicarbonyls and 1,2-diamines as precursor reagents. For designing Co3O4 nanocages, we employed a simple and scalable method involving Kirkendall effect in which thermal decomposition of Co3[Co(CN)6]2 was carried out thereafter, nanocages were loaded with Ni nanoparticles to obtain the final Ni@Co3O4 catalyst. Results revealed that Ni@Co3O4 catalyst possesses immense potential to accelerate condensation of diamines and di-carbonyls in absence of any additives under mild reaction conditions. The superior catalytic efficiency has been attributed to the hollow architecture of the nanocatalyst comprising of abundant catalytic sites. This protocol exhibits several remarkable attributes such as mild reaction conditions outstanding functional group tolerance, high yield, immense durability and reusability for six subsequent runs.
- Sharma, Aditi,Dixit, Ranjana,Sharma, Shivani,Dutta, Sriparna,Yadav, Sneha,Arora, Bhavya,Gawande, Manoj B.,Sharma, Rakesh K.
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- Microwave-Assisted Synthesis of Heterocycles from Aryldiazoacetates**
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Herein, we describe a rapid microwave-assisted, metal-free synthesis of substituted quinoxalinones and quinoxalines using the carbene-mediated reaction between aryldiazo esters and 1,2-diamines. The reaction can encompass a range of substituents and structural variations to afford quinoxalin-2-ones in 14–80 % yield and corresponding quinoxalines in good to excellent yields upon oxidation (67–96 %). The approach can be employed to generate symmetrical and unsymmetrical 2,3-diarylquinoxalines, bis-quinoxalines as well as novel quinoxaline-substituted diazo esters and should be a valuable addition to the heterocycle synthesis toolbox.
- Cousin, étienne,Elumalai, Vijayaragavan,Hansen, J?rn H.,Hansen, Stephanie R.,Kristoffersen, Tone,Starck, Eliot,Wagner, Lucille J.
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p. 7069 - 7078
(2020/11/30)
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- Synthesis method of quinoxaline heterocyclic derivative
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The invention discloses a synthesis method of a quinoxaline heterocyclic derivative. An intermolecular redox reaction and a condensation cyclization reaction are carried out on an o-nitroaniline compound and an o-diol compound under the action of a water-soluble alkali to prepare the quinoxaline heterocyclic derivative in one step. Expensive transition metal catalysts and ligands do not need to beused, the water-soluble alkali is used as an accelerant and can be removed in a water washing manner, so that the product has no transition metal residue, the product is easy to separate, the recovery rate is high, and the method is simple in condition, easy to operate and low in equipment requirement; and the water-soluble alkali is used as the accelerant, so the unique byproduct is water, the atom economy is high, and the method has good research and industrial application prospects.
- -
-
Paragraph 0070-0073
(2020/05/30)
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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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- Dowex 50W: Mild efficient reusable heterogeneous catalyst for synthesis of quinoxaline derivatives in aqueous medium
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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
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p. 1218 - 1224
(2021/02/09)
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- Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines
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We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.
- Niesobski, Patrik,Martínez, Ivette Santana,Kustosz, Sebastian,Müller, Thomas J. J.
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p. 5214 - 5218
(2019/07/31)
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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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- Ball-milling synthesized hydrotalcite supported Cu-Mn mixed oxide under solvent-free conditions: An active catalyst for aerobic oxidative synthesis of 2-acylbenzothiazoles and quinoxalines
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A rapid solvent-free ball-milling method was developed to prepare a hydrophobic hydrotalcite supported Cu-Mn mixed oxide catalyst (Cu-Mn/HT). The mechanochemically prepared catalyst exhibited high catalytic activity and recyclability towards the aerobic synthesis of 2-acylbenzothiazoles and quinoxalines in green medium ethanol compared with the ones synthesized via grinding and wet-impregnation. Moreover, control experiments showed that the catalyst was successfully used in green oxidative esterification and coupling as well. Cu-Mn/HT was characterized by BET, ICP, XRD, XPS, SEM and TEM, which indicated that more surface oxygen vacancies and formed CuMn2O4 species on HT might contribute to the catalytic activity.
- Meng, Xu,Bi, Xiuru,Yu, Chaoying,Chen, Gexin,Chen, Baohua,Jing, Zhenqiang,Zhao, Peiqing
-
supporting information
p. 4638 - 4644
(2018/10/23)
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- 2-Iodo benzoic acid: An unconventional precursor for the one pot multi-component synthesis of quinoxaline using organo Cu (II) catalyst
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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
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supporting information
p. 3657 - 3663
(2018/09/12)
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- Synthesis of quinoxalines through iodine-catalyzed one-pot annulation of alkynes with o-phenylenediamines
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The synthesis of N-heterocycles of quinoxalines has been developed by an efficient protocol of one-pot annulation of alkynes with o-phenylenediamines. A variety of quinoxalines were prepared in good to high yields in the presence of catalytic amount of iodine as a catalyst.
- Zi, Jing,Gu, Da-Wei,Zhang, Yan,Hu, Zhe-Yao,Zhang, Xing-Quan,Guo, Xun-Xiang
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supporting information
p. 915 - 920
(2018/03/21)
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- One-pot aqueous-phase synthesis of quinoxalines through oxidative cyclization of deoxybenzoins with 1,2-phenylenediamines catalyzed by a zwtterionic Cu(II)/calix[4]arene complex
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A green protocol for the synthesis of quinoxalines has been developed from catalytic oxidative cyclization of deoxybenzoins with 1,2-phenylenediamines in water. The optimal conditions are involved in the use of a water-soluble mononuclear copper(II) complex of a zwitterionic calix[4]arene [Cu(II)L(H2O)]I2 (1, H4L?=?[5,11,17,23–tetrakis (trimethylammonium)–25,26,27,28–tetrahydroxycalix[4]arene]) as a catalyst in alkali solution after refluxing for 15?h in O2. The target quinoxaline and its derivatives were obtained in good yields (up to 88%). The procedure described in this paper is simple, practical and environmentally benign.
- Gao, Jun,Ren, Zhi-Gang,Lang, Jian-Ping
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p. 1087 - 1092
(2017/05/22)
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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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- Yb/NaY molecular sieve catalyst to catalyze the synthesis method for ensuring
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The invention relates to a method for synthesizing a quinoxaline compound under catalysis of a Yb/NaY molecular sieve catalyst. The method specifically comprises the following steps of (a) mixing alpha-hydroxyketone, o-phenylenediamine, morpholine and the Yb/NaY molecular sieve catalyst, adding a solvent, and performing stirring and refluxing for 4 to 6 hours at 75 to 85 DEG C; (b) filtering the mixture obtained in the step (a), recycling a filter residue which is the Yb/NaY molecular sieve catalyst, and performing column chromatography separation on filtrate to obtain the quinoxaline compound. Compared with the prior art, a method for synthesizing the Yb/NaY molecular sieve catalyst is simple and metal load rate is high; the catalyst is high in thermal stability and easy to store and recycle; device characteristic detection shows that integrated molecular sieve pore passages and crystal structures of the catalyst are maintained; during condensation reaction between the alpha-hydroxyketone and the o-phenylenediamine under the catalysis of Yb/NaY, reaction conditions of are mild, simplicity in operation is ensured, the yield of a target product is 84 to 93 percent, and reduction in the cyclic catalysis efficiency of Yb/NaY is avoided.
- -
-
Paragraph 0062-0065
(2016/11/24)
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- Synthetic method of quinoxaline heterocyclic compound
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The invention provides a synthetic method of a quinoxaline heterocyclic compound. A quinoxaline heterocyclic derivative is prepared through one step by carrying out oxidation and cyclic condensation reaction on benzoin and ortho-diamine under the catalysis of a non-transition metal catalyst. According to the method, low-price and easily-available benzoin is used as a raw material, a water-soluble non-transition metal is used as a catalyst and convenient, economical and safe air is used as a direct oxidant to synthesize a target heterocyclic compound through one step at room temperature or a temperature slightly higher than the room temperature; the reaction condition is simple and mild; and inert gas protection is not needed as the synthesis is carried out in the air. The method is easy to operate, the only byproduct is water, the product is simple and easy to separate and purify, the yield is high, and the reaction condition requirement is relatively low, so that the method is wide in application range and has good research and industrial application prospects.
- -
-
Paragraph 0021; 0022
(2016/10/09)
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- In vitro and in vivo activities of 2,3-diarylsubstituted quinoxaline derivatives against Leishmania amazonensis
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Leishmaniasis is endemic in 98 countries and territories worldwide. The therapies available for leishmaniasis have serious side effects, thus prompting the search for new therapies. The present study investigated the antileishmanial activities of 2,3-diaryl-substituted quinoxaline derivatives against Leishmania amazonensis. The antiproliferative activities of 6,7-dichloro-2,3-diphenylquinoxaline (LSPN329) and 2,3-di-(4-methoxyphenyl)-quinoxaline (LSPN331) against promastigotes and intracellular amastigotes were assessed, and the cytotoxicities of LSPN329 and LSPN331 were determined. Morphological and ultrastructural alterations were examined by electron microscopy, and biochemical alterations, reflected by the mitochondrial membrane potential (ΔΨm), mitochondrial superoxide anion (O2.-) concentration, the intracellular ATP concentration, cell volume, the level of phosphatidylserine exposure on the cell membrane, cell membrane integrity, and lipid inclusions, were evaluated. In vivo antileishmanial activity was evaluated in a murine cutaneous leishmaniasis model. Compounds LSPN329 and LSPN331 showed significant selectivity for promastigotes and intracellular amastigotes and low cytotoxicity. In promastigotes, ultrastructural alterations were observed, including an increase in lipid inclusions, concentric membranes, and intense mitochondrial swelling, which were associated with hyperpolarization of ΔΨm, an increase in the O2.- concentration, decreased intracellular ATP levels, and a decrease in cell volume. Phosphatidylserine exposure and DNA fragmentation were not observed. The cellular membrane remained intact after treatment. Thus, the multifactorial response that was responsible for the cellular collapse of promastigotes was based on intense mitochondrial alterations. BALB/c mice treated with LSPN329 or LSPN331 showed a significant decrease in lesion thickness in the infected footpad. Therefore, the antileishmanial activity and mitochondrial mechanism of action of LSPN329 and LSPN331 and the decrease in lesion thickness in vivo brought about by LSPN329 and LSPN331 make them potential candidates for new drug development for the treatment of leishmaniasis.
- Kaplum, Vanessa,Cogo, Juliana,Sangi, Diego Pereira,Ueda-Nakamura, Tania,Corrêa, Arlene Gon?alves,Nakamura, Celso Vataru
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p. 3433 - 3444
(2016/07/06)
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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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- 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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- Synthesis of 2,4,5-trisubstituted imidazoles, quinoxalines and 1,5-benzodiazepines over an eco-friendly and highly efficient ZrO2-Al2O3 catalyst
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ZrO2-Al2O3 containing 80 mol% of ZrO2 was prepared by solution combustion, impregnation and precipitation methods. All the prepared catalytic materials were characterized by PXRD, NH3-TPD, N2 adsorption isotherms, FTIR, TEM, SEM, EDAX and ICP-OES techniques. These catalytic materials were used in a rapid, simple, versatile and efficient synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions at moderate temperature in shorter reaction time (20 min). This is achieved by three-component cyclo-condensation of benzil, aldehydes and ammonium acetate in excellent yields. The derivatives of quinoxalines and 1,5-benzodiazepines were synthesized effectively by cyclo-condensation of 1,2-diamine with α-diketones and carbonyl compound with O-phenylenediamines respectively over ZrO2-Al2O3 at moderate temperature (80 °C) for the reaction time of 20-40 min in presence of ethanol as a solvent. The present method is experimentally simple, non-toxic and involves inexpensive reagents, clean reaction pathways and an eco-friendly catalyst. The catalytic materials used can be easily separated from the reaction mixture and reused for several reaction cycles without much loss of catalytic activity.
- Thimmaraju,Shamshuddin, S. Z. Mohamed
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p. 60231 - 60243
(2016/07/11)
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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)
-
- SO3H-functionalized metal organic frameworks: An efficient heterogeneous catalyst for the synthesis of quinoxaline and derivatives
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An efficient alkylsulfonate functionalized metal organic framework (MOF), MIL-101-Cr-NH-RSO3H, has been successfully synthesized through a post-synthetic modification strategy of MIL-101-Cr-NH2 with 1,3-propanesultone reagent. The high surface area of the MIL-101-Cr-NH2 MOF guaranteed the high dispersion of -SO3H active species and the large pore size improved the contacting ability between the substrate and these active sites. The solid MIL-101-Cr-NH-RSO3H catalyst exhibited high catalytic performance in the preparation of quinoxaline derivatives by the condensation of benzene-1,2-diamines with 1,2-dicarbonyl compounds. Furthermore, the MIL-101-Cr-NH-RSO3H catalyst exhibits good stability, general applicability and excellent recycling performance.
- Andriamitantsoa, Radoelizo S.,Wang, Jingjing,Dong, Wenjun,Gao, Hongyi,Wang, Ge
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p. 35135 - 35143
(2016/05/09)
-
- Synthesis and application of polyvinylimidazole-based Br?nsted acidic ionic liquid grafted silica as an efficient heterogeneous catalyst in the preparation of quinoxaline derivatives
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Two types of polymer-grafted silica based on polyvinylimidazole Br?nsted acidic ionic liquids were prepared and used as new heterogeneous catalysts for the preparation of pharmaceutically important quinoxaline derivatives. These catalysts were characterized by thermogravimetric analysis, FT-IR spectroscopy, and titration. They could be recycled without considerable loss in their catalytic activity. High efficiency of the catalysts along with short reaction times, high yields, easy purification, recyclability, and simple procedure are among the advantages of these catalytic systems.
- Tamami, Bahman,Sardarian, Alireza,Ataollahi, Elaheh
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p. 422 - 433
(2016/07/06)
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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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- Synthesis of quinoxalines by a carbon nanotube-gold nanohybrid-catalyzed cascade reaction of vicinal diols and keto alcohols with diamines
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A one-pot oxidation-condensation method for the synthesis of quinoxalines from readily available benzoins or benzhydrols and 1,2-phenylenediamines or 2,3-diaminopyridine by use of a gold-carbon nanotube nanohybrid as a heterogeneous catalyst is reported. Quinoxalines are formed under mild conditions in air and in excellent yields. The simple and efficient methodology offers a safe and sustainable alternative to conventional acid and/or base-catalyzed thermal processes.
- Shah, Nimesh,Gravel, Edmond,Jawale, Dhanaji V.,Doris, Eric,Namboothiri, Irishi N. N.
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- Graphene oxide (GO) or reduced graphene oxide (rGO): Efficient catalysts for one-pot metal-free synthesis of quinoxalines from 2-nitroaniline
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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
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p. 6762 - 6767
(2016/01/30)
-
- Molecular design, synthesis and evaluation of 2,3-diarylquinoxalines as estrogen receptor ligands
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Selective Estrogen Receptor Modulators (SERMs) are characteristically capable of being antagonist and agonist of estrogen receptors and, therefore, they can inhibit or stimulate estrogen production in different tissues. Aiming to contribute to the identification of new synthetic SERMs candidates, the basic skeletons of raloxifene and tamoxifene were used as model. Here of, a set of 2,3-diaryl-quinoxalines having 2-(piperidin-1-yl)ethanol in the side chain have been synthesized and evaluated against human mammary carcinoma cells estrogen dependent (MCF-7), as well as in recombinant yeast assays (RYA) expressing estrogen receptor. Compound LSPN332 showed 40% inhibition of MCF-7 and EC50=290.6 μM in RYA. The efficient synthesis of 2,3-diarylquinoxalines represents an excellent opportunity to identify new SERMs, and should therefore be of interest to the medicinal chemistry community.
- Sangi, Diego P.,Cominetti, Márcia R.,Becceneri, Amanda B.,Resende, Flavia A.,Varanda, Eliana A.,Montanari, Carlos A.,Paix?o, Marcio W.,Corrêa, Arlene G.
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p. 736 - 746
(2015/12/01)
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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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- Synthesis and biological evaluation of novel 2,3-disubstituted quinoxaline derivatives as antileishmanial and antitrypanosomal agents
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Quinoxalines belong to the N-containing heterocyclic compounds that stand out as having promising biological activity due to their privileged scaffold. In this work, we report the synthesis, antileishmanial, and antitrypanosomal properties of 46 new 2,3-disubstituted quinoxaline and 40 previously reported derivatives. Among all of the compounds screened for in vitro activity against epimastigotes and trypomastigotes of Trypanosoma cruzi and promastigotes of Leishmania amazonensis as well as mammalian toxicity on LLCMK2 cells and J774 macrophages, analogues from series 5, 6, 7, 9, 12, and 13 displayed high activity at micromolar IC50 and EC50 concentrations. Sixteen quinoxaline derivatives were selected and evaluated on T. cruzi and/or L. amazonensis amastigotes. The most active compounds were 6a-b and 7d-e, on all evolutive forms of L. amazonensis and T. cruzi evaluated with IC50 values 0.1-0.8 1/4M on promastigotes and epimastigotes 1.4-8.6 on amastigotes. Compounds 5k, 12b and 13a were the most selective (SI Combining double low line 19.5-38.4) on amastigotes of T. cruzi. In general their activity was directly related to the methylsulfoxyl, methylsulfonyl, and amine groups as well as the presence of chorine or bromine in the molecules. The current results indicate that these quinoxaline derivatives are novel and promising agents for further development towards a treatment for Chagasg disease and leishmaniasis.
- Cogo, Juliana,Kaplum, Vanessa,Sangi, Diego Pereira,Ueda-Nakamura, Tania,Correa, Arlene Goncalves,Nakamura, Celso Vataru
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p. 107 - 123
(2015/03/18)
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- Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst
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A catalytic system comprising mesoporous silica functionalized with Cu(II)-DiAmSar was synthesized. This was demonstrated as an efficient heterogeneous catalyst for the synthesis of biologically useful pyridopyrazine and quinoxaline heterocycles under solvent-free conditions. X-ray diffraction, transmission electron microscopy, N2 adsorption-desorption, Fourtier transformation infrared spectroscopy, and thermogravimetric analysis were used to characterize the catalyst and investigate the texture of SBA-15 during the grafting process.
- Mohammadi, Marzieh,Bardajee, Ghasem Rezanejade,Pesyan, Nader Noroozi
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p. 1379 - 1386
(2015/09/01)
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- Nitrilotris(Methylenephosphonic Acid) as a New Highly Efficient and Recyclable Br?Nested Acid Catalyst for the Synthesis of Quinoxaline Derivatives under Mild and Green Conditions
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Nitrilotris(methylenephosphonic acid) has been introduced as a novel organocatalyst for the preparation of quinoxalines. It can efficiently catalyze the synthesis of quinoxaline derivatives from 1,2-diamines and 1,2-diketones under mild, efficient, and eco-friendly conditions. Excellent yields, very short reaction times, safety, and recyclability of the catalyst system are other features of the proposed method.
- Fathi, Safoura,Sardarian, Ali Reza
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p. 1471 - 1478
(2015/09/01)
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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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- Star-shaped Keggin-type heteropolytungstate nanostructure as a new catalyst for the preparation of quinoxaline derivatives
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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
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p. 1136 - 1143
(2015/02/05)
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- An iron Schiff base complex loaded mesoporous silica nanoreactor as a catalyst for the synthesis of pyrazine-based heterocycles
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An iron Schiff base complex was encapsulated in SBA-15 mesoporous silica to afford a Fe(III)-Schiff base/SBA-15 heterogeneous nanocatalyst for the synthesis of pyridopyrazine and quinoxaline heterocycles. These reactions proceeded in water with excellent yields. The catalyst was characterized by physico-chemical and spectroscopic methods and found to retain the characteristic channel structures of the SBA-15, allowing good accessibility of the encapsulated metal complex.
- Malakooti, Reihaneh,Bardajee, Ghasem Rezanejade,Hadizadeh, Somayyeh,Atashin, Hassan,Khanjari, Hadiseh
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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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- Synthesis and biological evaluation of novel 2,3-disubstituted quinoxaline derivatives as antileishmanial and antitrypanosomal agents
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Quinoxalines belong to the N-containing heterocyclic compounds that stand out as having promising biological activity due to their privileged scaffold. In this work, we report the synthesis, antileishmanial, and antitrypanosomal properties of 46 new 2,3-disubstituted quinoxaline and 40 previously reported derivatives. Among all of the compounds screened for in vitro activity against epimastigotes and trypomastigotes of Trypanosoma cruzi and promastigotes of Leishmania amazonensis as well as mammalian toxicity on LLCMK2 cells and J774 macrophages, analogues from series 5, 6, 7, 9, 12, and 13 displayed high activity at micromolar IC50 and EC50 concentrations. Sixteen quinoxaline derivatives were selected and evaluated on T. cruzi and/or L. amazonensis amastigotes. The most active compounds were 6a-b and 7d-e, on all evolutive forms of L. amazonensis and T. cruzi evaluated with IC50 values 0.1-0.8 μM on promastigotes and epimastigotes 1.4-8.6 on amastigotes. Compounds 5k, 12b and 13a were the most selective (SI = 19.5-38.4) on amastigotes of T. cruzi. In general their activity was directly related to the methylsulfoxyl, methylsulfonyl, and amine groups as well as the presence of chorine or bromine in the molecules. The current results indicate that these quinoxaline derivatives are novel and promising agents for further development towards a treatment for Chagasg € disease and leishmaniasis.
- Cogo, Juliana,Kaplum, Vanessa,Sangi, Diego Pereira,Ueda-Nakamura, Tnia,Corra, Arlene Gonalves,Nakamura, Celso Vataru
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p. 107 - 123
(2015/01/08)
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- Assisted tandem catalytic cross metathesis-oxidation: In one flask from styrenes to 1,2-diketones and further to quinoxalines
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1,2-Diketones were synthesized from styrenes by combining a cross metathesis and a Ru-catalyzed alkene oxidation to an assisted tandem catalytic sequence. The synthesis relies on the use of just one metathesis precatalyst, which was in situ converted to the oxidation catalyst by addition of an alkyl hydroperoxide as a chemical trigger and oxidant. The one-flask sequence can be extended beyond 1,2-diketones to quinoxalines, by condensation of the oxidation products with ortho-phenylenediamine.
- Schmidt, Bernd,Krehl, Stefan,Hauke, Sylvia
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p. 5427 - 5435
(2013/07/25)
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- Zirconium schiff-base complex modified mesoporous silica as an efficient catalyst for the synthesis of nitrogen containing pyrazine based heterocycles
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Zirconium Schiff-base complex modified SBA-15 was synthesized and characterized by powder X-ray diffraction (XRD), BET nitrogen adsorption-desorption methods, IR spectroscopy and thermogravimetric analysis. The XRD and BET analyses show that textural properties of SBA-15 were retained during the grafting procedure. The modified SBA was successfully applied as a heterogeneous catalyst for the synthesis of a library of nitrogen containing pyrazine based heterocycles in good to excellent yields in water media.
- Malakooti, Reihaneh,Bardajee, Ghasem Rezanejade,Mahmoudi, Hesamaldin,Kakavand, Nahale
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p. 853 - 861
(2013/08/23)
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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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- 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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- Poly(N,N ′-dibromo-N-ethyl-benzene-1,3-disulphonamide) and N,N,N ′,N ′-tetrabromobenzene-1,3- disulphonamide as novel catalysts for synthesis of quinoxaline derivatives
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Poly(N,N ′ -dibromo-N-ethyl-benzene-1,3-disulphonamide) [PBBS] and N,N,N ′,N ′ -tetrabromobenzene-1,3- disulphonamide [TBBDA] were used as efficient catalysts for the synthesis of quinoxaline derivatives in excellent yields from 1,2-diamines and 1,2-dicarbonyls under aqueous and solvent-free conditions. [Figure not available: see fulltext.]
- Ghorbani-Vaghei, Ramin,Hajinazari, Somaye
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p. 353 - 358
(2013/07/26)
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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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- 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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- 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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- 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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- A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
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A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.
- Mamedov, Vakhid A.,Zhukova, Nataliya A.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Beschastnova, Tat'Yana N.,Adgamova, Dil'Bar I.,Samigullina, Aida I.,Latypov, Shamil K.
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supporting information
p. 1403 - 1416
(2013/02/23)
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- ZrOCl2.8H2O in water: An efficient catalyst for rapid one-pot synthesis of pyridopyrazines, pyrazines and 2,3-disubstituted quinoxalines
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Zirconium(IV) oxide chloride was found to be a rapid and efficient catalyst for the synthesis of pyrazines and 2,3-disubstituted quinoxalines in water. A variety of pyridopyrazine and 2,3-disubstituted quinoxaline derivatives are readily prepared in high yields under green conditions by cyclocondensation of the desired 1,2-diamine and 1,2-diketone using a catalytic amount of zirconium(IV) oxide chloride in water. Less active diamines, such as 2,3- and 3,4-diaminopyridines took part in this protocol to provide the desired products in good to excellent yields.
- Bardajee, Ghasem Rezanejade
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p. 872 - 877
(2013/10/22)
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