- A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation
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A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.
- Gullapelli, Kumaraswamy,Brahmeshwari,Ravichander
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- Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement
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A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.
- Li, Shichen,Feng, Lei,Ma, Chen
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p. 9320 - 9323
(2021/06/14)
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- PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions
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A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is
- Ding, Chengcheng,Feng, Kaili,Li, Shichen,Ma, Chen
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p. 5542 - 5548
(2021/08/16)
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- Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties
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A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.
- Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto
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p. 13613 - 13623
(2021/08/23)
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- Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(iii) catalysis
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Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO3 or CO2. Furthermore, some control experiments are conducted to elucidate the reaction mechanism. This journal is
- Hu, Fang-Peng,Zhang, Xue-Guo,Wang, Meng,Wang, He-Song,Huang, Guo-Sheng
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p. 11980 - 11983
(2021/12/01)
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- Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2- a ]quinoxalines from 2-(1 H -Pyrrol-1-yl)anilines and Alkylboronic Acids
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A radical pathway for the construction of pyrrolo[1,2- a ]quinoxalines by using 2-(1 H -pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operat
- Guan, Xin,Yan, Rulong
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p. 359 - 362
(2020/02/27)
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- Ruthenium-Catalyzed Synthesis of Pyrrolo[1,2- A [quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Sulfoxonium Ylides
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A ruthenium-catalyzed [5+1] annulation of 1-(2-aminophenyl)pyrroles with α-carbonyl sulfoxonium ylides is reported. This reaction provides a one-step method for synthesizing pyrrolo[1,2- A [quinoxaline derivatives under ambient conditions. The system proceeds with a short reaction time and a high functional-group tolerance. Notably, this divergent protocol tolerates β-keto sulfoxonium ylides and can be applied to α-ester sulfoxonium ylides. A preliminary study was made of the mechanism of the reaction, and a reaction pathway is proposed.
- Cui, Xin-Feng,Hu, Fang-Peng,Huang, Guo-Sheng,Zhan, Zhen-Zhen,Zhou, Xiao-Qiang
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p. 1205 - 1210
(2020/07/20)
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- Unexpected activated carbon-catalyzed pyrrolo[1,2-a]quinoxalines synthesis in water
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An interesting and recyclable activated carbon/water catalytic system for efficient synthesis of pyrrolo[1,2-a]quinoxaline derivatives was developed. The intramolecular C–N and C–C bond can be easily constructed in water under mild condition. This reaction features a broad substrate scope, a good tolerance to water and air, metal-free, additive-free and redox reagent-free.
- Sun, Qi,Liu, Liyan,Yang, Yu,Zha, Zhenggen,Wang, Zhiyong
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p. 1379 - 1382
(2019/05/04)
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- TFAA-Catalyzed Annulation Synthesis of Spiro Pyrrolo[1,2-a]quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Benzoquinones/Ketones
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A metal-free trifluorosulfonate anhydride (TFAA)-catalyzed strategy for the synthesis of spiro pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and benzoquinones/ketones has been developed. With this general method, spiro pyrrolo[1,2-a]quinoxalin
- Ni, Jixiang,Jiang, Yong,Qi, Zhenjie,Yan, Rulong
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supporting information
p. 2898 - 2902
(2019/08/12)
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- A new pathway to pyrrolo[1,2-a]quinoxalines via solvent-free one-pot strategy utilizing FeMoSe nanosheets as efficient recyclable synergistic catalyst
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FeMoSe nanocatalyst was synthesized using solvothermal approach from readily available precursors, namely Mo(CO)6, FeSO4 and Se, and characterized by spectroscopic and microscopic analyses. The FeMoSe material offered high catalytic
- To, Tuong A.,Nguyen, Chuc T.,Tran, My H.P.,Huynh, Thai Q.,Nguyen, Tung T.,Le, Nhan T.H.,Nguyen, Anh D.,Tran, Phong D.,Phan, Nam T.S.
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p. 163 - 173
(2019/08/02)
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- Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters
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A copper-catalyzed tandem ring-opening/cyclization reaction for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters has been developed. This reaction involves C-C bond cleavage and C-C and C-N bond constructions with good functional group tolerance. A wide range of products are obtained in moderate to good yields under mild conditions.
- An, Zhenyu,Jiang, Yong,Guan, Xin,Yan, Rulong
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p. 10738 - 10741
(2018/09/29)
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- Molybdenum-catalyzed synthesis of nitrogenated polyheterocycles from nitroarenes and glycols with reuse of waste reduction byproduct
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A novel domino reduction/imine formation/intramolecular cyclization/oxidation for the efficient synthesis of pyrrolo(indolo)[1,2-a]quinoxalines and pyrrolo(indolo)-[3,2-c]-quinolines from readily available nitrobenzenes and glycols is reported. The process utilizes the carbonyl byproduct of the initial dioxomolybdenum(VI)-catalyzed reduction of nitroaromatics with glycols as a reagent for the imine generation. This method represents the first sustainable domino reaction for the preparation of biologically relevant heterocycles that internally incorporates the waste formed in the first step to the final product.
- Rubio-Presa, Ruben,Pedrosa, Maria R.,Fernandez-Rodríguez, Manuel A.,Arnaiz, Francisco J.,Sanz, Roberto
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p. 5470 - 5473
(2017/11/06)
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- FeCl3-Catalyzed synthesis of pyrrolo[1,2-: A] quinoxaline derivatives from 1-(2-aminophenyl)pyrroles through annulation and cleavage of cyclic ethers
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A straightforward Fe-catalyzed method for the synthesis of pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclic ethers, which includes functionalization of C(sp3)-H bonds and the construction of C-C and C-N bonds, has been devel
- An, Zhenyu,Zhao, Lianbiao,Wu, Mingzhong,Ni, Jixiang,Qi, Zhenjie,Yu, Guiqin,Yan, Rulong
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p. 11572 - 11575
(2017/10/27)
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- An environmentally friendly approach to pyrrolo[1,2-a]quinoxalines using oxygen as the oxidant
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We have developed an environmentally benign and practical protocol for the synthesis of pyrrolo[1,2-a]quinoxalines, which represent ubiquitous structural units common to a number of biologically active compounds. This synthetic system features simple operation and using clean oxidant, as well as mild reaction conditions. Both aromatic and aliphatic aldehydes can be used for the reaction and the products were obtained in good to excellent yields.
- Wang, Chao,Li, Yun,Zhao, Jianfei,Cheng, Bin,Wang, Huifei,Zhai, Hongbin
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supporting information
p. 3908 - 3911
(2016/08/09)
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- Harnessing the pyrroloquinoxaline scaffold for FAAH and MAGL interaction: Definition of the structural determinants for enzyme inhibition
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This paper describes the development of piperazine and 4-aminopiperidine carboxamides/carbamates supported on a pharmacogenic pyrroloquinoxaline scaffold as inhibitors of the endocannabinoid catabolizing enzymes fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). Structure-activity relationships and molecular modelling studies allowed the definition of the structural requirements for dual FAAH/MAGL inhibition and led to the identification of a small set of derivatives (compounds 5e, i, k, m) displaying a balanced inhibitory profile against both enzymes, with compound 5m being the frontrunner of the subset. Favorable calculated physico-chemical properties suggest further investigation for specific analogues.
- Brindisi, Margherita,Brogi, Simone,Maramai, Samuele,Grillo, Alessandro,Borrelli, Giuseppe,Butini, Stefania,Novellino, Ettore,Allarà, Marco,Ligresti, Alessia,Campiani, Giuseppe,Di Marzo, Vincenzo,Gemma, Sandra
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p. 64651 - 64664
(2016/07/23)
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- Efficient synthesis of pyrrolo[1,2-: A] quinoxalines catalyzed by a Br?nsted acid through cleavage of C-C bonds
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An efficient and convenient one-pot domino reaction for the direct synthesis of pyrrolo[1,2-a]quinoxalines has been developed. This approach utilizes an imine formation reaction, SEAr reaction and cleavage of C-C bonds catalyzed by a Br?nsted acid. β-Diketones and β-keto esters are both well tolerated to give the corresponding products in moderate to excellent yields.
- Xie, Caixia,Feng, Lei,Li, Wanli,Ma, Xiaojun,Ma, Xinkun,Liu, Yihan,Ma, Chen
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supporting information
p. 8529 - 8535
(2016/09/28)
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- Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-A] quinoxalines as new antiplasmodial agents
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Thanks to a preliminary in vitro screening of several CCl 3-substituted-nitrogen containing heterocycles belonging to our chemical library, the 2-trichloromethylquinoxaline scaffold appeared to be of potential interest for developing new antiplasmodial agents. Then, combining these experimental results to the antimalarial properties reported for various pyrrolo[1,2-A]quinoxaline derivatives, an original series of fifteen 7-substituted-4-trichoromethylpyrrolo[1,2-A]quinoxalines was synthesized in a 4 to 5 reaction steps pathway. All molecules were evaluated in vitro toward both their antiplasmodial activity on the K1 multi-resistant Plasmodium falciparum strain and their cytotoxicity on the HepG2 human cell line. Thus, 3 hit molecules were identified, displaying IC50 values in the micromolar range and low cytotoxicity values, reaching good selectivity indexes, in comparison with the reference drugs chloroquine and doxycycline. Structure-activity relationship studies showed that the pyrrolo[1,2-A] quinoxaline scaffold can support selective antiplasmodial activity when substituted at position 4 by a CCl3 group. However, substitution at position 7 of the same scaffold is neither beneficial for cytotoxicity nor favourable for the solubility in the biological media.
- Primas, Nicolas,Suzanne, Peggy,Verhaeghe, Pierre,Hutter, Sébastien,Kieffer, Charline,Laget, Michèle,Cohen, Anita,Broggi, Julie,Lancelot, Jean-Charles,Lesnard, Aurélien,Dallemagne, Patrick,Rathelot, Pascal,Rault, Sylvain,Vanelle, Patrice,Azas, Nadine
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- Discovery of pyrrolo-benzo-1,4-diazines as potent Nav1.7 sodium channel blockers
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A series of pyrrolo-benzo-1,4-diazine analogs have been synthesized and displayed potent Nav1.7 inhibitory activity and moderate selectivity over Nav1.5. The syntheses, structure-activity relationships, and selected pharmacokinetic data of these analogs are described. Compound 41 displayed anti-nociceptive efficacy in the rat CFA pain model at 100 mpk oral dosing.
- Ho, Ginny D.,Tulshian, Deen,Bercovici, Ana,Tan, Zheng,Hanisak, Jennifer,Brumfield, Stephanie,Matasi, Julius,Heap, Charles R.,Earley, William G.,Courneya, Brandy,Jason Herr,Zhou, Xiaoping,Bridal, Terry,Rindgen, Diane,Sorota, Steve,Yang, Shu-Wei
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p. 4110 - 4113
(2014/11/07)
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- A rapid and efficient synthesis of a new pyrrolobenzodiazocines via an intramolecular Friedel-Crafts reaction
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New pyrrolobenzodiazocines 3 have been prepared by an intramolecular Friedel-Crafts process from pyrrolobenzoacrylamides 2. The cyclisation process involving a 1,4-intramolecular addition of a pyrrole onto acrylamide led to the formation of an eight-membe
- BouzBouz, Samir,Sanselme, Morgane
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p. 5884 - 5887
(2010/01/11)
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- Synthesis of omeprazole analogues and evaluation of these as potential inhibitors of the multidrug efflux pump NorA of Staphylococcus aureus
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A series of 11 pyrrolo[1,2-α]quinoxaline derivatives, 1a to 1k, sharing structural analogies with omeprazole, a eukaryotic efflux pump inhibitor (EPI) used as an antiulcer agent, was synthesized. Their inhibitory effect was evaluated using Staphylacoccus aureus strain SA-1199B overexpressing NorA. By determinations of the MIC of norfloxacin in the presence of these EPIs devoid of intrinsic antibacterial activity and used at 128 μg/ml, and by the checkerboard method, compound 1e (MIC decrease, 16-fold; fractional inhibitory concentration index [ΣFIC], 0.18) appeared to be more active than compounds 1b to 1d, reserpine, and omeprazole (MIC decrease, eightfold; ΣFIC, 0.31), followed by compounds 1a and 1f (MIC decrease, fourfold; ΣFIC, 0.37) and 1g to 1k (MIC decrease, twofold; ΣFIC, 0.50 to 0.56). By time-kill curves combining norfloxacin (1/4 MIC) and the most efficient EPIs (128 μg/ml), compound 1e persistently restored the bactericidal activity of norfloxacin (inoculum reduction, 3 log10 CFU/ml at 8 and 24 h), compound If led to a delayed but progressive decrease in the number of viable cells, and compounds 1b to 1d and omeprazole acted synergistically (inoculum reduction, 3 log10 CFU/ml at 8 h but further regrowth), while compound 1a and reserpine slightly enhanced norfloxacin activity. The bacterial uptake of norfloxacin monitored by high-performance liquid chromatography confirmed that compounds 1a to 1f increased antibiotic accumulation, as did reserpine and omeprazole. Since these EPIs did not disturb the Δψ and ΔpH, they might directly interact with the pump. A structure-activity relationships study identified the benzimidazole nucleus of omeprazole as the main structural element involved in efflux pump inhibition and highlighted the critical role of the chlorine substituents in the stability and efficiency of compounds 1e to 1f. However, further pharmacomodulation is required to obtain therapeutically applicable derivatives. Copyright
- Vidaillac, Celine,Guillon, Jean,Arpin, Corinne,Forfar-Bares, Isabelle,Ba, Boubakar B.,Grellet, Jean,Moreau, Stephane,Caignard, Daniel-Henri,Jarry, Christian,Quentin, Claudine
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p. 831 - 838
(2007/10/03)
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- Synthesis of new pyrrolo[l,2-a]quinoxalines: Potential non-peptide glucagon receptor antagonists
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Synthesis of new pyrrolo[1,2-a]quinoxaline derivatives was achieved starting from various nitroanilines or orthophenyle-nediamines. Their affinity towards glucagon receptors was evaluated. Elsevier, Paris.
- Guillon, Jean,Dallemagne, Patrick,Pfeiffer, Bruno,Renard, Pierre,Manechez, Dominique,Kervran, Alain,Rault, Sylvain
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p. 293 - 308
(2007/10/03)
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- Synthesis of New Phenylpyrrolylpyrroles
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A series of methyl or ethyl 3-(N-arylpyrrol-2-yl)-1H-pyrrole-2-carboxylates and 2,4-dicarboxylates has been synthesized using an alkyl isocyanides addition-cyclization to N-arylpyrrole derivatives such as carboxaldehydes and nitropropenes.
- Dumoulin, H.,Rault, S.,Robba, M.
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p. 1703 - 1707
(2007/10/03)
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- Synthesis of 5,6-Dihydropyrrolothiadiazocines
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The title compounds 15-18 and 26 are prepared by intramolecular cyclisation of the pyrrolylthiols derived from sodium borohydride reduction of N-aryl-2-thiocyanatopyrroles 11-14 and 25.
- Cheeseman, G. W. H.,Hawi, A. A.,Varvounis, G.
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p. 423 - 427
(2007/10/02)
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- Spiro(pyrrolo (1,2-A)quinoxalines)
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Spiro[pyrrolo(1,2-a)quinoxalines] and their physiologically tolerable acid addition salts possessing anticonvulsant and central nervous system depressant properties, and a process for their preparation are described.
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