- In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
-
Substituted quinoxaline derivatives are traditionally synthesized by co-condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o-phenylenediamine and 1,2-diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo-condensation reaction followed by obtaining the aforesaid nitrogen-containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.
- Tamuli, Kashyap J.,Nath, Shyamalendu,Bordoloi, Manobjyoti
-
supporting information
p. 983 - 1002
(2021/02/27)
-
- Synthesis, biological evaluation, and in silico studies of new acetylcholinesterase inhibitors based on quinoxaline scaffold
-
A quinoxaline scaffold exhibits various bioactivities in pharmacotherapeutic interests. In this research, twelve quinoxaline derivatives were synthesized and evaluated as new acetyl-cholinesterase inhibitors. We found all compounds showed potent inhibitory activity against acetyl-cholinesterase (AChE) with IC50 values of 0.077 to 50.080 μM, along with promising predicted drug-likeness and blood–brain barrier (BBB) permeation. In addition, potent butyrylcholinesterase (BChE) inhibitory activity with IC50 values of 14.91 to 60.95 μM was observed in some compounds. Enzyme kinetic study revealed the most potent compound (6c) as a mixed-type AChE inhibitor. No cytotoxicity from the quinoxaline derivatives was noticed in the human neuroblastoma cell line (SHSY5Y). In silico study suggested the compounds preferred the peripheral anionic site (PAS) to the catalytic anionic site (CAS), which was different from AChE inhibitors (tacrine and galanthamine). We had proposed the molecular design guided for quinoxaline derivatives targeting the PAS site. Therefore, the quinoxaline derivatives could offer the lead for the newly developed candidate as potential acetylcholinesterase inhibitors.
- Khongkow, Pasarat,Lomlim, Luelak,Nualnoi, Teerapat,Saetang, Jirakrit,Suwanhom, Paptawan,Tipmanee, Varomyalin
-
-
- Organocatalytic Green Approach Towards the Fabrication of Fused Benzo N,N-containing Heterocycles Facilitated by Ultrasonic Irradiation
-
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
-
-
- Ionic liquid functionalized cellulose as an efficient heterogeneous catalyst for the facile and green synthesis of benzoxazine, pyrazine and quinoxaline derivatives in aqueous media
-
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
-
p. 1517 - 1524
(2016/07/06)
-
- An experimental and theoretical study of intramolecular regioselective oxidations of 6-substituted 2,3-dimethylquinoxaline derivatives
-
An experimental and theoretical study of the regioselective Riley oxidation was conducted on a series of 2,3-dimethyl-6-substituted-quinoxalines bearing EWG (NO2, CN, CF3, Cl, Br, F, COOH, COOMe, COPh) and EDG (2,3-dimethylquinoxaline, OMe, OH, NH2) substituents. The nitrogen lone pair of electrons of the symmetric benzopyrazine moiety initiates the oxidation and promotes nucleophilic competition between the two active sites to give carbaldehyde regioisomers a and b. The mesomeric effect provides the dominant contribution to the regioselectivity. The compounds were characterized by NMR, measuring the 1H, 13C, pfg-HSQC, pfg-HMBC, and 15N, 1H correlation signals established by pfg-HMQC. The nucleophilic reactivity of nitrogen was evaluated by 1H NMR titration and analyzed using Perrin linearization to determine the reactivity ratio, ΔK, of the N4 and N1 nitrogen atoms. The structures were optimized using density functional theory at the ωB97XD/6-311G++(d,p) level of theory. The highest occupied molecular orbitals modeled using the HF/6-311G++(d,p) functionals revealed an asymmetric electron density that confirmed the asymmetric nucleophilicity of the nitrogen centers. These values agreed with the experimentally measured ΔK ratios. The PM6 theoretical calculations of the heats of formation of the mesomeric forms and intermediates of (2,3-dimethyl-6-substituted-quinoxalines)-SeO2 allowed us to identify the reaction routes that minimized energy expenditures. The regioselectivities were explained in terms of the energetic diagrams of the regioisomers. All compounds evaluated indicated a preference toward forming regioisomer b, except for the derivative bearing the EDG substituent (2,3-dimethylquinoxaline) which displayed a preference for regioisomer a.
- Peralta-Cruz, Javier,Díaz-Fernández, Mónica,ávila-Castro, Alberto,Ortegón-Reyna, David,Ariza-Castolo, Armando
-
p. 5501 - 5515
(2016/07/06)
-
- A zirconium Schiff base complex immobilized on starch-coated maghemite nanoparticles catalyzes heterogeneous condensation of 1,2-diamines with 1,2-dicarbonyl compounds
-
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
-
p. 205 - 211
(2016/02/20)
-
- New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models
-
Parkinson's disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, we have designed and synthesized a second-generation of quinoxaline-derived molecules based on structure-activity relationship studies, which led previously to the discovery of our first neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of our newly synthesized quinoxaline-derived compounds has led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder.
- Le Douaron, Gael,Ferrié, Laurent,Sepulveda-Diaz, Julia E.,Amar, Majid,Harfouche, Abha,Séon-Méniel, Blandine,Raisman-Vozari, Rita,Michel, Patrick P.,Figadère, Bruno
-
p. 6169 - 6186
(2016/07/26)
-
- Ferrocene-quinoxaline Y-shaped chromophores as fascinating second-order NLO building blocks for long lasting highly active SHG polymeric films
-
The first example of a Y-shaped ferrocene quinoxaline derivative with a surprisingly high and stable second harmonic generation (SHG) response in composite polymeric films is reported. The interesting quadratic hyperpolarizability values of different substituted Y-shaped chromophores are also investigated in solution by the EFISH technique.
- Senthilkumar, Kabali,Thirumoorthy, Krishnan,Dragonetti, Claudia,Marinotto, Daniele,Righetto, Stefania,Colombo, Alessia,Haukka, Matti,Palanisami, Nallasamy
-
supporting information
p. 11939 - 11943
(2016/08/05)
-
- Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst
-
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
-
p. 1379 - 1386
(2015/09/01)
-
- Aqueous hydrofluoric acid catalyzed facile synthesis of 2,3,6-substituted quinoxalines
-
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
-
p. 1504 - 1508
(2015/04/27)
-
- Nano SbCl5.SiO2: An efficient catalyst for the synthesis of quinoxaline derivatives at room temperature under solventless condition
-
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
-
p. 2851 - 2856
(2015/06/02)
-
- 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
-
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
-
p. 1471 - 1478
(2015/09/01)
-
- A novel protocol for selective synthesis of monoclinic zirconia nanoparticles as a heterogeneous catalyst for condensation of 1,2-diamines with 1,2-dicarbonyl compounds
-
ZrO2 nanocatalyst has been obtained successfully using novel and safe agents through a simple and safe sol-gel method (polymerizing-complexing) and characterized by XRD, FT-IR, Raman spectroscopies and transmission electron microscopy (TEM). Raman spectroscopies and XRD results indicated only formation of monoclinic zirconia. TEM images revealed spherical nanoparticles with 20-40 nm diameter range. The spectral and analysis data confirmed the effectiveness of the method for preparation of monoclinic zirconia by preventing grain growth or agglomeration of particles. The nanostructured ZrO2 exhibited high efficiency in catalyzing condensation of various 1,2-diamine and 1,2-dicarbonyl compounds for the synthesis of heterocyclic compounds. The recovery of the title heterogeneous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk one.
- Jafarpour, Maasoumeh,Rezapour, Elham,Ghahramaninezhad, Mahboobe,Rezaeifard, Abdolreza
-
p. 676 - 682
(2014/02/14)
-
- Zirconium schiff-base complex modified mesoporous silica as an efficient catalyst for the synthesis of nitrogen containing pyrazine based heterocycles
-
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
-
p. 853 - 861
(2013/08/23)
-
- Reusable α-MoO3 nanobelts catalyzes the green and heterogeneous condensation of 1,2-diamines with carbonyl compounds
-
Crystalline nanobelts of α-MoO3 have been obtained successfully using novel and safe agents through a simple and safe sol-gel method (polymerizing-complexing) and characterized by XRD, FT-IR, Raman spectroscopies, high resolution transmission electron microscopy (HRTEM), scanning electron microscopy (SEM) and the temperature programmed desorption (TPD) of ammonia. An orthorhombic lattice system for nano-MoO3 was established. The HRTEM images showed that the nanobelt morphology of α-MoO3 mostly ranged from 20-70 nm in width and 200-400 nm in length. The ammonia TPD profile demonstrated strong acidic sites. The spectral and analysis data confirmed the effectiveness of the method for the preparation of α-MoO3 nanobelts by prevention of grain growth or agglomeration of the particles. The nanostructured MoO3 exhibited a high efficiency in catalyzing the condensation reaction of various 1,2-diamine and carbonyl compounds for synthesis of heterocyclic compounds. The recovery of the title heterogenous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk material.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Ghahramaninezhad, Mahboube,Tabibi, Tooba
-
p. 2087 - 2095
(2013/10/08)
-
- A reusable zirconium(IV) Schiff base complex catalyzes highly efficient synthesis of quinoxalines under mild conditions
-
A zirconium(IV) complex of a bidentate Schiff base (ZrL2Cl 2) has been synthesized by the reaction of (z)-N-benzylidene-2- hydroxypropane-1-amine (HL) and ZrCl4. Spectroscopic data and elemental analyses are consistent with a monomeric complex with a ligand:Zr ratio of 2:1. The catalytic activity of ZrL2Cl2 has been investigated for the efficient synthesis of a wide variety of quinoxaline derivatives under mild conditions. The employment of ethanol as an environmentally benign solvent in this high yield method, along with high turnover numbers and reusability of the catalyst providing ready scalability, makes it appropriate for practical applications.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Haddad, Reza,Gazkar, Somayeh
-
-
- Microwave-assisted synthesis of quinoxaline derivatives using glycerol as a green solvent
-
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
-
p. 1244 - 1247
(2014/03/21)
-
- Sustainable approach to tandem catalysis: Expedient access to quinoxalines and pyrido[2,3-b]pyrazines from α-hydroxyketones via microwave-induced [(NH4)6Mo7O24·4H 2O - PEG 300] polar paste catalyst system
-
[(NH4)6Mo7O24·4H 2O-PEG 300] is introduced as a polar paste catalyst system for tandem synthesis of quinoxalines and pyrido[2,3-b]pyrazines under open-vessel focused microwave irradiation. Low conversions were obtained when catalyst or PEG was used individually. Accordingly, a convenient combination of catalyst and PEG mostly led to quantitative yield of products within 15 min microwave irradiation with good turnover frequency values (11-20 h-1) taking a tandem process into consideration. The salient features of this environmentally benign method are fast conversions, high product selectivity and the use of a low-cost, readily available, nontoxic, catalyst and medium.
- Aghapoor, Kioumars,Mohsenzadeh, Farshid,Mohebi Morad, Mina,Darabi, Hossein Reza
-
p. 764 - 767
(2012/10/29)
-
- FeCl3 and morpholine as efficient cocatalysts for the one-step synthesis of quinoxalines from α-hydroxyketones and 1,2-diamines
-
One-step conversion including intramolecular hydrogen bond decomposition, aerobic oxidation, and condensation from α-hydroxyketones and 1,2-diamines into quinoxalines is reported using FeCl3 and morpholine as cocatalysts. Taylor & Francis Group, LLC.
- Liu, Peng,Lei, Min,You, Hanyun,Chen, Xubing,Chen, Hu,Ma, Lei,Hu, Lihong
-
experimental part
p. 236 - 245
(2011/11/06)
-
- Glycerin and CeCl3 7H2O: A new and efficient recyclable reaction medium for the synthesis of quinoxalines
-
An efficient and environmentally benign process for the synthesis of quinoxalines has been developed using glycerine-cerium chloride as a reaction medium. This method is applicable to a variety of diketones and 1,2-phenylenediamines to afford the corresponding quinoxaline derivatives in excellent yields. The reaction medium was recovered and reused for further reactions without any problem. Taylor & Francis Group, LLC.
- Venkat Narsaiah,Kranthi Kumar
-
experimental part
p. 883 - 892
(2012/03/11)
-
- Perturbing pro-survival proteins using quinoxaline derivatives: A structure-activity relationship study
-
In HeLa cells the combinatorial knockdown of Bcl-xL and Mcl-1 is sufficient to induce spontaneous apoptosis. Quinoxaline derivatives were screened for the induction of Mcl-1 dependent apoptosis using a cell line without functional Bcl-xL. Quinoxaline urea
- Rajule, Rajkumar,Bryant, Vashti C.,Lopez, Hernando,Luo, Xu,Natarajan, Amarnath
-
scheme or table
p. 2227 - 2234
(2012/06/01)
-
- Heterogeneous SnCl2/SiO2 versus homogeneous SnCl 2 acid catalysis in the benzo[N,N]-heterocyclic condensation
-
The scope of homogeneous Lewis acid-catalyzed benzo[N,N]-heterocyclic condensation was expanded to include the use of various metal salts not reported in the literature and SnCl2·2H2O was finally selected. Among various solid supports activated with SnCl2, heterogeneous SnCl2/SiO2 proved to be the most effective and significantly higher conversions were achieved compared to SnCl 2·2H2O itself. The results of TG-DTA and BET indicated that dispersed SnCl2 coordinates with surface hydroxyl groups of silica leading to formation of stable Lewis acid sites. Low catalyst loading, operational simplicity, practicability and applicability to various substrates render this eco-friendly approach as an interesting alternative to previously applied procedures.
- Darabi, Hossein Reza,Aghapoor, Kioumars,Mohsenzadeh, Farshid,Jalali, Mohammad Reza,Talebian, Shiva,Ebadi-Nia, Leila,Khatamifar, Ehsan,Aghaee, Ali
-
experimental part
p. 213 - 218
(2011/11/06)
-
- Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions
-
Alumina as a cheap, heterogeneous and reusable catalyst can provide environmentally friendly alternatives for synthesis of quinoxaline derivatives via condensation of 1,2-diamines and 1,2-dicarbonyl compounds under solvent-free conditions. The products could be separated simply from catalyst by filtration and the catalyst could be recycled and reused for several times without noticeably decreasing in catalytic activity.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Danehchin, Maryam
-
experimental part
p. 48 - 51
(2011/12/16)
-
- Vitamin B1 as a metal-ion-free natural catalyst for sustainable quinoxaline ring condensation under sonochemical conditions
-
The role of vitamin B1 as a catalyst is investigated for the quinoxaline ring condensation under various mild reaction conditions. The results revealed that the combination of vitamin B1 and ultrasonic irradiation promotes the reaction more efficiently. The salient features of this environmentally benign method are fast conversions, excellent yields for a wide range of substrates, and the use of a low-cost, readily available, nontoxic, and metal-ion-free natural catalyst. The wide range of turnover frequency values (6-400 h-1) shows that the reaction rate is highly dependent on the nature of the functional groups on the aromatic ring of substrates. Moreover, a plausible mechanism for the catalytic action of vitamin B1 has been introduced.
- Aghapoor, Kioumars,Mohsenzadeh, Farshid,Talebian, Shiva,Tehrani, Mohammad Jafar,Balavar, Yadollah,Khanalizadeh, Golriz,Darabi, Hossein Reza
-
experimental part
p. 619 - 624
(2012/01/15)
-
- Microwave-assisted synthesis of quinoxalines in peg-400
-
A rapid and efficient procedure for the synthesis of quinoxaline derivatives has been achieved by condensation of aryl-1,2-diamines with 1,2-dicarbonyl compounds catalyzed by polyethylene glycol under CEM-focused microwave-irradiation conditions. Copyright
- Zhang, Xia-Zhong,Wang, Jin-Xian,Bai, Lin
-
experimental part
p. 2053 - 2063
(2011/07/07)
-
- 2,3-Substituted quinoxalin-6-amine analogs as antiproliferatives: A structure-activity relationship study
-
The quinoxaline core is considered a privileged scaffold as it is found in a variety of biologically relevant molecules. Here we report the synthesis of a quinoxalin-6-amine library, screening against a panel of cancer cell lines and a structure-activity
- Chen, Qianyi,Bryant, Vashti C.,Lopez, Hernando,Kelly, David L.,Luo, Xu,Natarajan, Amarnath
-
supporting information; experimental part
p. 1929 - 1932
(2011/04/24)
-
- Nano-BF3·SiO2: A reusable and eco-friendly catalyst for synthesis of quinoxalines
-
2,3-Disubstituted quinoxalines were synthesized via condensation of α-diketones and 1,2-phenylenediamines. Nano-BF3·SiO 2 as a "green" and reusable solid acid was used as the catalyst for the synthesis of quinoxalines. The reaction was carried out at room temperature under sonication with high to excellent yields.
- Mirjalili,Bamoniri,Akbari
-
experimental part
p. 487 - 491
(2012/01/13)
-
- Nano-TiO2: An eco-friendly alternative for the synthesis of quinoxalines
-
Nano-TiO2 as an eco-friendly and efficient nanocatalyst was applied for quinoxaline preparation with improved yield. In this protocol, diketones and 1,2-diamines were condensed in the presence of catalyst at room temperature.
- Mirjalili, Bi Bi Fatemeh,Akbari, Ali
-
experimental part
p. 753 - 756
(2012/01/05)
-
- Synthesis of quinoxalines in presence of zinc triflate
-
A simple and efficient method for the synthesis of quinoxaline derivatives has been developed. The reactions were carried out in presence of zinc triflate in acetonitrile reflux. The method is applicable to a variety of diketones and 1,2-phenylenediamines to afford the corresponding derivatives in excellent yields.
- Subrahmanyam, C. Siva,Narayanan
-
experimental part
p. 1331 - 1333
(2011/12/21)
-
- Zirconium(IV) chloride as versatile catalyst for the expeditious synthesis of quinoxalines and pyrido[2,3-b]pyrazines under ambient conditions
-
Among the various transition metal chlorides, zirconium(IV) chloride was found to be an efficient catalyst for the rapid synthesis of a wide range of 2,3-dialkyl- and 2,3-diaryl-quinoxaline and pyrido[2,3-b]pyrazine derivatives in excellent yields at room temperature. The remarkable features of this catalytic process are the mild reaction conditions, quantitative yields, short reaction times, high conversions, tolerability of various functional groups, clean reaction profiles, and operational simplicity. Graphical Abstract: Among the various transition metal chlorides, zirconium(IV) chloride was found to be an efficient catalyst for the rapid synthesis of a wide range of 2,3-dialkyl- and 2,3-diaryl-quinoxaline and pyrido[2,3-b]pyrazine derivatives in excellent yields at room temperature. The remarkable features of this catalytic process are the mild reaction conditions, quantitative yields, short reaction times, high conversions, tolerability of various functional groups, clean reaction profiles, and operational simplicity.
- Aghapoor, Kioumars,Darabi, Hossein Reza,Mohsenzadeh, Farshid,Balavar, Yadollah,Daneshyar, Hesam
-
experimental part
p. 49 - 53
(2011/12/14)
-
- Synthesis of quinoxaline derivatives catalyzed by PEG-400
-
Polyethylene glycol (PEG) was found to be an effective catalyst for the condensation of 1,2-diamines with 1,2-dicarbonyl compounds to afford the corresponding quinoxaline derivatives in excellent yields under mild reaction conditions.
- Zhang, Xia Zhong,Wang, Jin Xian,Sun, Yong Jun,Zhan, Hong Wen
-
experimental part
p. 395 - 398
(2010/12/24)
-
- Magnetic Fe3O4 nanoparticles as new, efficient, and reusable catalysts for the synthesis of quinoxalines in water
-
A novel, environmentally friendly procedure has been developed for the synthesis of quinoxaline derivatives in the presence of magnetic Fe 3O4 nanoparticles. The reaction between 1,2-diamines and 1,2-dicarbonyl compounds was carried out in water to afford quinoxaline derivatives in high yield. The catalyst can be recovered by the use of an external magnet and reused for five cycles with almost consistent activity. CSIRO 2010.
- Lue, Hong-Yan,Yang, Shu-Hong,Deng, Jia,Zhang, Zhan-Hui
-
experimental part
p. 1290 - 1296
(2011/04/15)
-
- Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines
-
A series of 29 new quinoxalines was synthesized and evaluated in vitro against several parasites (Leishmania donovani, Trypanosoma brucei brucei, and Trichomonas vaginalis). Several of them displayed interesting activities, and particularly four quinoxaline amides showed in vitro antileishmanial properties (IC50 less than 20 μM).
- Hui, Xu,Desrivot, Julie,Bories, Christian,Loiseau, Philippe M.,Franck, Xavier,Hocquemiller, Reynald,Figadere, Bruno
-
p. 815 - 820
(2007/10/03)
-