- Synthesis, characterization and application of α-Ca3 (PO4)2 as a heterogeneous catalyst for the synthesis of 2.3-diphenylquinoxaline derivatives and knoevenagel condensation under green conditions
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Green chemistry is now paramount in modern life and industrial sector. It has become a research priority and a scientific challenge. In this study, alpha-tricalcic phosphate was prepared as a green catalytic medium. This medium has been characterized by v
- Anahmadi, Haddou,Benzekri, Zakaria,Boukhris, Said,El hajri, Fatima,El youbi, Mohamed Salahdine,Fathi, Majda,Idrissi, Brahim Chafik El,Sibous, Sarra,Souizi, Abdelaziz
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- Thiazolo[5,4-f]quinoxalines, Oxazolo[5,4-f]quinoxalines and Pyrazino[b,e]isatins: Synthesis from 6-Aminoquinoxalines and Properties
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The regioselective iodination of different 2-mono-, 3-mono- and 2,3-disubstituted 6-aminoquinoxalines, which takes place at their 5-position, was rationalized on the basis of Hückel theory calculations. Oxazolo- and thiazolo[5,4-f]quinoxaline analogues of
- Bach, Stéphane,Dorcet, Vincent,El Osmani, Nour,Erb, William,Fajloun, Ziad,Lassagne, Frédéric,Mongin, Florence,Mongin, Olivier,Picot, Laurent,Richy, Nicolas,Robert, Thomas,Roisnel, Thierry,Sims, Joshua M.,Thiéry, Valérie
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supporting information
p. 2756 - 2763
(2021/06/25)
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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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- Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives
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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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- Structure activity relationship (SAR) study identifies a quinoxaline urea analog that modulates IKKβ phosphorylation for pancreatic cancer therapy
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Genetic models validated Inhibitor of nuclear factor (NF) kappa B kinase beta (IKKβ) as a therapeutic target for KRAS mutation associated pancreatic cancer. Phosphorylation of the activation loop serine residues (S177, S181) in IKKβ
- Sagar, Satish,Singh, Sarbjit,Mallareddy, Jayapal Reddy,Sonawane, Yogesh A.,Napoleon, John V.,Rana, Sandeep,Contreras, Jacob I.,Rajesh, Christabelle,Ezell, Edward L.,Kizhake, Smitha,Garrison, Jered C.,Radhakrishnan, Prakash,Natarajan, Amarnath
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- An efficient method for the synthesis of quinoxaline derivatives catalyzed by titanium silicate-1
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Abstract: A series of quinoxaline derivatives were efficiently synthesized by convenient and simple procedure in excellent yields using 1 wt.% of titanium silicate (TS-1) catalyzed reaction of 1,2-diamines and 1,2-diketones in methanol at room temperature
- Chandrachood, Pranav S.,Jadhav, Amol R.,Garud, Dinesh R.,Deshpande, Nirmala R.,Puranik, Vedavati G.,Kashalkar, Rajashree V.
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p. 5219 - 5230
(2020/09/18)
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- A green solid acid catalyst 12-tungstophosphoric acid H3[PW12O40] supported on g-C3N4 for synthesis of quinoxalines
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A green Keggin-type heteropoly-12-tungstophosphoric acid, (H3[PW12O40].12H2O) supported on graphitic carbon nitride g-C3N4 (HPW/g-C3N4-40), was developed for one-pot s
- Kumaresan, Murugan,Saravanan, Vadivel,Sami, Ponnusamy,Swaminathan, Meenakshisundaram
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p. 4193 - 4209
(2020/07/08)
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- [BBSA-DBN][HSO4]: a novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines
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Abstract: A novel –SO3H difunctionalized Bronsted acidic ionic liquid (BAIL) 1, 5-bis (butanesulphonic acid)-diazobicyclo [4,3,0] non-5-enium hydrogen sulphate [BBSA-DBN][HSO4] is introduced for efficient synthesis of quinoxalines vi
- Patil, Megha U.,Shinde, Sachinkumar K.,Patil, Sandip P.,Patil, Suresh S.
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p. 4923 - 4938
(2020/08/24)
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- HBTU-catalyzed simple and mild protocol for the synthesis of quinoxaline derivatives
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HBTU-catalyzed, simple, mild, and effective protocol for the synthesis of quinoxalines has been established. The reaction between 1,2-diamines, benzil, and catalytic amount of HBTU in ethanol resulted into quinoxalines. Various aliphatic, aromatic and het
- Bhushan, B. Popatkar,Gangadhar, A. Meshram
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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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- Manganese(I)-Catalyzed Sustainable Synthesis of Quinoxaline and Quinazoline Derivatives with the Liberation of Dihydrogen
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Direct synthesis of N-heterocycles via the acceptorless dehydrogenative coupling is very challenging and scarcely reported under 3d transition-metal catalysis. Here, we have developed an efficient Mn(I)-catalyzed sustainable synthesis of various quinoxalines from 1,2-diaminobenzenes and 1,2-diols via the acceptorless dehydrogenative coupling reaction. Further, this strategy was successfully applied for the unprecedented synthesis of quinazolines by the reaction of 2-aminobenzyl alcohol with primary amides. The present protocol provides an atom-economical and sustainable route for the synthesis of various quinoxaline and quinazoline derivatives by employing an earth-abundant manganese salt and simple phosphine-free NNN-tridentate ligand.
- Mondal, Akash,Sahoo, Manoj Kumar,Subaramanian, Murugan,Balaraman, Ekambaram
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p. 7181 - 7191
(2020/07/21)
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- An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives
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A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship between the catalytic activity and acidity was discussed. It was also found that among the all ILs, [Bmim]CF3SO3 was the most effective, eco-friendly and less expensive solvent and catalyst for the above etiquette. This method is of significant value due to the eco-friendly nature of ionic liquid and non usage of separate catalyst to drive the reaction forward. The protocol proves to be efficient and environmentally benign in terms of good to excellent yields, low reaction times, simple work-up, ease of recovery, and reusability of ionic liquid for six times.
- Bhargava, Sangeeta,Soni,Rathore, Deepti
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- Organocatalytic Green Approach Towards the Fabrication of Fused Benzo N,N-containing Heterocycles Facilitated by Ultrasonic Irradiation
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The development of a metal-free protocol for transformations in organic synthesis offers a significant potential environmental benefit. This article reports the exploration of meglumine, a nontoxic and biodegradable amino sugar, as an organocatalyst for the synthesis of biologically active 1H-dibenzo[b,e][1,4]diazepin-1-ones, highly regioselective benzimidazole derivatives and derivatives of quinoxalines. Operational simplicity, mild reaction conditions, shorter reaction times, and use of green solvents are the highlights of this protocol. The advantage of ultrasonic irradiation has been significantly explored for the synthesis of the aforesaid compounds. Furthermore, the multifaceted use of o-phenylenediamine has also been accentuated in the study.
- Nongrum, Ridaphun,Kharmawlong, George Kupar,Rani, Jims World Star,Rahman, Noimur,Dutta, Arup,Nongkhlaw, Rishanlang
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- Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One-Pot Synthesis of Imines and Quinoxalines
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Three copper(I) complexes, [CuCl(L)(PPh3)2] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh3)2Cu(μ-Cl)2Cu(PPh3)] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1H NMR, 13C NMR and 31P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to catalyse the one-pot synthesis of imines and quinoxalines. Heterogenized catalyst (4) was prepared by reacting more active complex 3 with polystyrene supported triphenylphosphane, and characterized by elemental analyses, and DRS-UV, FT-IR, ICP-OES, and solid-state NMR techniques. Catalytic activity of the complexes (3 and 4) was tested in the formation of imines from alcohols and amines, and quinoxalines from hydroxy ketones and diamines. Heterogeneity and reusability of catalyst 4 were evaluated, and the catalyst can be reused for four runs without any loss in activity.
- Sindhuja, Dharmalingam,Vasanthakumar, Punitharaj,Bhuvanesh, Nattamai,Karvembu, Ramasamy
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p. 3588 - 3596
(2019/08/20)
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- Phosphine free Mn-complex catalysed dehydrogenative C-C and C-heteroatom bond formation: A sustainable approach to synthesize quinoxaline, pyrazine, benzothiazole and quinoline derivatives
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Herein the first sustainable synthesis of quinoxalines, pyrazines and benzothiazoles catalysed by a phosphine free Mn(i) complex via acceptorless dehydrogenative coupling (ADC) is reported. This method is also applied successfully to synthesize quinolines via the dehydrogenation (removal of H2) and condensation (removal of H2O) reaction between 2-aminobenzyl alcohols and secondary alcohols.
- Das, Kalicharan,Mondal, Avijit,Srimani, Dipankar
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supporting information
p. 10582 - 10585
(2018/09/25)
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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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- 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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- ZnO-loaded mesoporous silica (KIT-6) as an efficient solid catalyst for production of various substituted quinoxalines
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Conventional homogeneous and microporous heterogeneous catalysts for quinoxalines production from diamines and diketones usually suffer from difficult separation or harsh reaction conditions. Here, we demonstrate the production of various substituted quin
- Hamid, Oveisi,Chari, M. Adharvana,Van Nguyen, Chi,Chen, Jeffrey E.,Alshehri, Saad M.,Yanmaz, Ekrem,Hossain, Shahriar A.,Yamauchi, Yusuke,Wu, Kevin C.-W.
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p. 111 - 115
(2016/12/30)
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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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- 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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- One-step approach for the synthesis of functionalized quinoxalines mediated by T3P-DMSO or T3P: Via a tandem oxidation-condensation or condensation reaction
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An easy and efficient propylphosphonic anhydride (T3P)-DMSO or T3P mediated oxidation-condensation or condensation reaction for the synthesis of quinoxalines derived from the interaction of different arrays of condensing partners with ortho-phenylene diamines (o-PDs) under simple and mild reaction conditions in one step has been reported for the first time.
- Harsha, Kachigere B.,Rangappa, Kanchugarkoppal S.
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p. 57154 - 57162
(2016/07/07)
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- Synthesis of 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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- Ionic liquid functionalized cellulose as an efficient heterogeneous catalyst for the facile and green synthesis of benzoxazine, pyrazine and quinoxaline derivatives in aqueous media
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Immobilization of acidic ionic liquid, 1-methyl-3-(3-trimethoxysilylpropyl) imidazolium hydrogen sulfate on cellulose (Cell-[pmim]HSO4) as an efficient heterogenous catalyst for the simple and environmentally benign synthesis of benzoxazine, pyrazine and quinoxaline derivatives in aqueous media at room temperature is described. The catalyst was characterized by FTIR spectroscopy and X-ray diffraction pattern. This method provides several advantages such as mild reaction conditions, environmentally friendly catalyst, good to excellent yields and simple work-up procedure.
- Moghaddam, Sevil Vaghefi,Valizadeh, Hassan
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p. 1517 - 1524
(2016/07/06)
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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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- 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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- Aqueous hydrofluoric acid catalyzed facile synthesis of 2,3,6-substituted quinoxalines
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A versatile synthetic route for the preparation of 2,3,6-trisubstituted quinoxalines in excellent yield is developed from θ-diamines and 1,2-dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures.
- Chandra Shekhar,Ravi Kumar,Sathaiah,Raju,Srinivas,Shanthan Rao,Narsaiah
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p. 1504 - 1508
(2015/04/27)
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- An efficient and recyclable nanoparticle-supported cobalt catalyst for quinoxaline synthesis
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The syntheses of quinoxalines derived from 1,2-diamine and 1,2-dicarbonyl compounds under mild reaction conditions was carried out using a nanoparticle-supported cobalt catalyst. The supported nanocatalyst exhibited excellent activity and stability and it
- Rajabi, Fatemeh,Alves, Diego,Luque, Rafael
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p. 20709 - 20718
(2015/12/23)
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- Synthesis, characterization and catalytic activity of oxovanadium(IV) complexes of heterocyclic acid hydrazones
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Two acid hydrazones, furan-2-carbaldehyde nicotinic hydrazone (L1) and furan-2-carbaldehyde benzhydrazone (L2) have been synthesized and they are characterized by elemental analysis, IR, NMR and UV spectral analysis. Oxovanadium(IV) complexes of these two
- Pandey, Manju,Sunaja Devi,Sreeja
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p. 4135 - 4137
(2015/12/23)
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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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- 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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- Protic ionic liquids: A lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans
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Protic ionic liquids (PILs), which are easily produced through the combination of a Bronsted acid and Bronsted base, such as [Mim]Ac and 1,4-diazabicyclo[ 2.2.2]octane (DABCO):AcOH:H2O (1:1:3), were found to be lucid, tunable tool for synthesis
- Mulik,Chandam,Patil,Patil,Mulik,Salunkhe,Deshmukh
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p. 10085 - 10096
(2016/01/12)
-
- 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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- 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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- Design, synthesis and biological evaluation of novel fluorinated heterocyclic hybrid molecules based on triazole & quinoxaline scaffolds lead to highly potent antimalarials and antibacterials
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A series of novel fluorinated heterocyclic hybrid molecules based on triazole & quinoxaline scaffold were designed, synthesized and evaluated for inhibition of Plasmodium falciparum, a virulent human malaria parasite. Mono and bis triazole tagged quinoxal
- Chandra Shekhar, Adimulam,Venkat Lingaiah, Boddupally Pedda,Shanthan Rao, Pamulaparthy,Narsaiah, Banda,Aparna Devi, Allanki,Sijwali, Puran Singh
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p. 393 - 407
(2015/06/22)
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- Saccharin as an organocatalyst for quinoxalines and pyrido[2,3-b[pyrazines Syntheses
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A room-temperature procedure using saccharin as catalyst has been described for the cyclocondensation of different 1,2-arylenediamines with various 1,2-dicarbonyl compounds, yielding either quinoxalines or pyrido[2,3-b] pyrazines. The reactions proceed in very short reaction times in methanol, and the target heterocycles are isolated in quantitative yields after addition of water, filtration, and drying. Substituted pyrido[2,3-b]pyrazines can also be reached regioselectively by reacting α-ketoaldehydes with 2,3-diaminopyridine. Taylor and Francis Group, LLC.
- Lassagne, Frederic,Chevallier, Floris,Mongin, Florence
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supporting information
p. 141 - 149
(2013/11/06)
-
- 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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- Emergence of pyrido quinoxalines as new family of antimalarial agents
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A series of novel N-alkyl dihydro pyrido quinoxaline derivatives were synthesized using Gould-Jacobs reaction and evaluated their antimalarial activity in vitro against chloroquine sensitive (3D7) and drug resistant (Dd2) strains of Plasmodium falciparum.
- Chandra Shekhar,Shanthan Rao,Narsaiah,Allanki, Aparna Devi,Sijwali, Puran Singh
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p. 280 - 287
(2014/04/03)
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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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- L-Proline mediated synthesis of quinoxalines; Evaluation of cytotoxic and antimicrobial activity
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A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employing l-proline as a catalyst in water. To the best of our knowledge this transformation is achieved for the first time using an organic catalyst. A small library of quinoxaline-sulphonamide conjugates have been synthesized using this protocol. The newly synthesized conjugates have been tested for their cytotoxicity and antimicrobial activity against several bacterial strains including one fungal strain. The majority of the compounds have exhibited significant cytotoxicity as well as antimicrobial activity. Compounds 5a, 5b and 5d were found to be promising with respect to both cytotoxicity and antimicrobial activity. This journal is
- Kamal, Ahmed,Babu, Korrapati Suresh,Faazil, Shaikh,Hussaini, S. M. Ali,Shaik, Anver Basha
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p. 46369 - 46377
(2015/02/19)
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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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- 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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- 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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- 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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- 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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- Microwave-assisted synthesis of quinoxaline derivatives using glycerol as a green solvent
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A rapid, efficient, and reliable catalyst-free procedure for the synthesis of quinoxaline derivatives in glycerol under focused microwave irradiation was developed. The reaction proceeded in glycerol without any catalyst making this methodology valuable from both economic and environmental viewpoints.
- Zhou,Zhang,Sun,Wang,Wang,Bai
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p. 1244 - 1247
(2014/03/21)
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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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- 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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- 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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