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Journal articles on the topic 'Quinoxalinones'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Awad, Ibrahim M. A., and Khairy M. Hassan. "Studies in Vilsmeier-Haack reaction. Application to quinoxalinones." Collection of Czechoslovak Chemical Communications 55, no. 11 (1990): 2715–21. http://dx.doi.org/10.1135/cccc19902715.

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The 3-methyl group in quinoxalinones I and II has been found to undergo diformylation by Vilsmeier reagent to give the corresponding aminoacrolein derivatives (III, IV). Condensation and/or interaction of III or IV with some secondary heterocyclic amines and/or with hydrazine, phenylhydrazine and hydroxylamine affords the related 3-methyl-N-(1H)-2-quinoxalinone and 1,3-dimethyl-2-quinoxalinone derivatives (VII-XVIII), some with pronounced fluorescence activities. All synthesized compounds have been screened in vitro for their antimicrobial activities against Gram-positive and Gram-negative bac

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2

Lv, Min, and Hui Xu. "The Combinatorial Synthesis of Bioactive Quinoxalines, Quinoxalinones and Quinoxalinols." Combinatorial Chemistry & High Throughput Screening 13, no. 3 (2010): 293–301. http://dx.doi.org/10.2174/138620710790980513.

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3

Toonchue, Saowanee, Ladawan Sumunnee, Khamphee Phomphrai, and Sirilata Yotphan. "Metal-free direct oxidative C–C bond coupling of pyrazolones and quinoxalinones." Organic Chemistry Frontiers 5, no. 12 (2018): 1928–32. http://dx.doi.org/10.1039/c8qo00328a.

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An efficient oxidative dehydrogenative coupling of quinoxalinones and pyrazolones has been successfully developed using a readily available persulfate oxidant. This protocol provides facile access to a wide array of hydroxy-pyrazolyl quinoxalinones in good to excellent yields.

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4

Lv, Min, and Hui Xu. "ChemInform Abstract: The Combinatorial Synthesis of Bioactive Quinoxalines, Quinoxalinones and Quinoxalinols." ChemInform 41, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.201028227.

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5

Song, J. H., S. M. Bae, H. Y. Shin, D. I. Jung, and J. H. Cho. "Synthesis of Spirohydantoins and Schiff Bases of Indenoquinoxalinones and Indenopyridopyrazinones." Asian Journal of Chemistry 32, no. 8 (2020): 1925–30. http://dx.doi.org/10.14233/ajchem.2020.22679.

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The main structure of many compounds containing spirohydantoin and Schiff bases of indenoquinoxalines and indenopyridopyrazinones expose valuable pharmacological properties. Herein, an effective synthesis and stereochemistry of indenoquinoxalinones (2a, 2b+bi~2d+di) and indenopyridopyrazinones (2e+ei~g+gi) via the reaction of ninhydrin with desirable diamines is reported. We synthesized the corres-ponding spirohydantoins (3a, 3b~d and 3bi~di) from synthesized indeno[1,2-b]quinoxalinones and indeno[1,2-b]pyrido[3,2-e]pyrazinones with the standard Bucherer-Bergs conditions (KCN, ammonium carbona

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6

Lian, Fei, Kun Xu, Wei Meng, Haonan Zhang, Zhoumei Tan, and Chengchu Zeng. "Nickel-catalyzed electrochemical reductive decarboxylative coupling of N-hydroxyphthalimide esters with quinoxalinones." Chemical Communications 55, no. 97 (2019): 14685–88. http://dx.doi.org/10.1039/c9cc07840a.

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7

Guo, Tao, Chuan-Chuan Wang, Xiang-Heng Fu, Yu Liu, and Pan-Ke Zhang. "Copper-catalyzed C–H/N–H cross-coupling reactions for the synthesis of 3-heteroaryl quinoxalin-2(1H)-ones." Organic & Biomolecular Chemistry 17, no. 13 (2019): 3333–37. http://dx.doi.org/10.1039/c9ob00294d.

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8

Renault, Kévin, Pierre-Yves Renard, and Cyrille Sabot. "Photophysical properties of quinoxalin-2(1H)-ones: application in the preparation of an azide-based fluorogenic probe for the detection of hydrogen sulfide." New Journal of Chemistry 41, no. 18 (2017): 10432–37. http://dx.doi.org/10.1039/c7nj01893b.

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9

Mtiraoui, Hasan, Kevin Renault, Morgane Sanselme, Moncef Msaddek, Pierre-Yves Renard, and Cyrille Sabot. "Correction: Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones." Organic & Biomolecular Chemistry 15, no. 35 (2017): 7474–75. http://dx.doi.org/10.1039/c7ob90126g.

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10

Zhang, Xu, Bin Xu, and Ming-Hua Xu. "Rhodium-catalyzed asymmetric arylation of N- and O-containing cyclic aldimines: facile and efficient access to highly optically active 3,4-dihydrobenzo[1,4]oxazin-2-ones and dihydroquinoxalinones." Organic Chemistry Frontiers 3, no. 8 (2016): 944–48. http://dx.doi.org/10.1039/c6qo00191b.

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11

Xu, Jun, Lin Huang, Lei He, et al. "Direct para-C–H heteroarylation of anilines with quinoxalinones by metal-free cross-dehydrogenative coupling under an aerobic atmosphere." Green Chemistry 23, no. 17 (2021): 6632–38. http://dx.doi.org/10.1039/d1gc01899j.

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12

Chen, Mu-Wang, Zhihong Deng, Qin Yang, Jian Huang, and Yiyuan Peng. "Enantioselective synthesis of trifluoromethylated dihydroquinoxalinones via palladium-catalyzed hydrogenation." Organic Chemistry Frontiers 6, no. 6 (2019): 746–50. http://dx.doi.org/10.1039/c8qo01361f.

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A highly enantioselective palladium-catalyzed asymmetric hydrogenation of 3-(trifluoromethyl)quinoxalinones has been successfully developed, providing a general and facile access to chiral 3-(trifluoromethyl)-3,4-dihydroquinoxalinones with up to 99% ee.

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13

Zhou, Kai, Ming Bao, Jingjing Huang, et al. "Iron-catalyzed [3 + 2]-cycloaddition of in situ generated N-ylides with alkynes or olefins: access to multi-substituted/polycyclic pyrrole derivatives." Organic & Biomolecular Chemistry 18, no. 3 (2020): 409–14. http://dx.doi.org/10.1039/c9ob02571e.

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An iron-catalyzed three-component reaction of benzimidazoles with diazoacetates and electron-deficient alkynes or alkenes that delivers multi-substituted pyrroles, pyrrolo[1,2-a]benzimidazoles and pyrrolo[1,2-a] quinoxalinones has been reported.

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14

Zhao, Zi-Biao, Xiang Li, Mu-Wang Chen, Zongbao K. Zhao, and Yong-Gui Zhou. "Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts." Chemical Communications 56, no. 53 (2020): 7309–12. http://dx.doi.org/10.1039/d0cc03091k.

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Using ureas as transfer catalysts through hydrogen bonding activation, biomimetic asymmetric reduction of benzoxazinones and quinoxalinones has been developed, giving chiral products with high enantioselectivities. A key dihydroquinoxalinone intermediate of a BRD4 inhibitor was synthesized using biomimetic asymmetric reduction.

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15

Krchňák, Viktor, Lajos Szabo, and Josef Vágner. "A solid phase traceless synthesis of quinoxalinones." Tetrahedron Letters 41, no. 16 (2000): 2835–38. http://dx.doi.org/10.1016/s0040-4039(00)00297-5.

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16

Carta, A., S. Piras, G. Loriga, and G. Paglietti. "Chemistry, Biological Properties and SAR Analysis of Quinoxalinones." Mini-Reviews in Medicinal Chemistry 6, no. 11 (2006): 1179–200. http://dx.doi.org/10.2174/138955706778742713.

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17

Rampont-Placidi, Valérie, Benoit Cossec, Marie-Thérèse Brondeau, and Pierre Mutzenhardt. "Complete13C and1H spectral assignments of certain substituted quinoxalinones." Magnetic Resonance in Chemistry 36, no. 4 (1998): 300–302. http://dx.doi.org/10.1002/(sici)1097-458x(199804)36:4<300::aid-omr170>3.0.co;2-c.

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18

Yotphan, Sirilata, Medena Noikham, and Tanakorn Kittikool. "Iodine-Catalyzed Oxidative Cross-Dehydrogenative Coupling of Quinoxalinones and Indoles: Synthesis of 3-(Indol-2-yl)quinoxalin-2-one under Mild and Ambient Conditions." Synthesis 50, no. 12 (2018): 2337–46. http://dx.doi.org/10.1055/s-0037-1609445.

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A highly efficient iodine-catalyzed oxidative cross-dehydrogenative coupling reaction of quinoxalinones and indoles has been developed. Without the requirement of peroxide and acid, this reaction utilizes a catalytic amount of molecular iodine to facilitate the C–C bond formation under ambient air. This simple and easy-to-handle protocol represents an interesting synthetic alternative with a good scope and functional group compatibility.

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19

Tung, Chieh-Li, and Chung-Ming Sun. "Liquid phase synthesis of chiral quinoxalinones by microwave irradiation." Tetrahedron Letters 45, no. 6 (2004): 1159–62. http://dx.doi.org/10.1016/j.tetlet.2003.12.056.

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20

Zhou, Jiadi, Peng Zhou, Tingting Zhao, Quanlei Ren, and Jianjun Li. "(Thio)etherification of Quinoxalinones under Visible‐Light Photoredox Catalysis." Advanced Synthesis & Catalysis 361, no. 23 (2019): 5371–82. http://dx.doi.org/10.1002/adsc.201901008.

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21

Shen, Chien-Hung, Chih-Chung Tseng, Cheng-Hsun Tasi, Suhas A. Shintre, Li-Hsun Chen, and Chung-Ming Sun. "Traceless polymer-supported divergent synthesis of quinoxalinones by microwave irradiation." Tetrahedron 68, no. 18 (2012): 3532–40. http://dx.doi.org/10.1016/j.tet.2012.03.015.

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22

Luo, Xuehong, Etienne Chenard, Peter Martens, Yun-Xing Cheng, and Mirosław J. Tomaszewski. "Practical Synthesis of Quinoxalinones via Palladium-Catalyzed Intramolecular N-Arylations." Organic Letters 12, no. 16 (2010): 3574–77. http://dx.doi.org/10.1021/ol101454x.

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23

Wang, Liping, Hongyun Liu, Fanfan Li, Jiquan Zhao, Hong‐Yu Zhang, and Yuecheng Zhang. "Copper‐Catalyzed C3−H Difluoroacetylation of Quinoxalinones with Ethyl Bromodifluoroacetate." Advanced Synthesis & Catalysis 361, no. 10 (2019): 2354–59. http://dx.doi.org/10.1002/adsc.201900066.

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24

AWAD, I. M. A., and K. M. HASSAN. "ChemInform Abstract: Studies in Vilsmeier-Haack Reaction. Application to Quinoxalinones." ChemInform 22, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199110193.

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25

Masand, Vijay H., Nahed N. Elsayed, Sumersingh D. Thakur, Nandkishor Gawhale, and Mithilesh M. Rathore. "Quinoxalinones Based Aldose Reductase Inhibitors: 2D and 3D‐QSAR Analysis." Molecular Informatics 38, no. 8-9 (2019): 1800149. http://dx.doi.org/10.1002/minf.201800149.

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26

Paul, Sanjay, Hari Datta Khanal, Chayan Dhar Clinton, Sung Hong Kim, and Yong Rok Lee. "Pd(TFA)2-catalyzed direct arylation of quinoxalinones with arenes." Organic Chemistry Frontiers 6, no. 2 (2019): 231–35. http://dx.doi.org/10.1039/c8qo01250d.

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27

Krchňák, Viktor, Jennifer Smith, and Josef Vágner. "Solid-Phase Traceless Synthesis of Selected Nitrogen-Containing Heterocyclic Compounds. The Encore Technique for Directed Sorting of Modular Solid Support." Collection of Czechoslovak Chemical Communications 66, no. 7 (2001): 1078–106. http://dx.doi.org/10.1135/cccc20011078.

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The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to c

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28

Ager, Ian R., Alan C. Barnes, Geoffrey W. Danswan, et al. "Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles." Journal of Medicinal Chemistry 31, no. 6 (1988): 1098–115. http://dx.doi.org/10.1021/jm00401a009.

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29

Sakata, Gozyo, Kenzi Makino, and Katsushi Morimoto. "The Facile One Pot Synthesis of 6-Substituted 2(1H)-Quinoxalinones." HETEROCYCLES 23, no. 1 (1985): 143. http://dx.doi.org/10.3987/r-1985-01-0143.

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30

Baumann, Marcus, Ian Baxendale, Christian Hornung, Steven Ley, Maria Rojo, and Kimberley Roper. "Synthesis of Riboflavines, Quinoxalinones and Benzodiazepines through Chemoselective Flow Based Hydrogenations." Molecules 19, no. 7 (2014): 9736–59. http://dx.doi.org/10.3390/molecules19079736.

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31

Patel, Mona, Robert J. McHugh, Beverly C. Cordova, et al. "Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors." Bioorganic & Medicinal Chemistry Letters 10, no. 15 (2000): 1729–31. http://dx.doi.org/10.1016/s0960-894x(00)00321-8.

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32

Sumunnee, Ladawan, Chaleena Pimpasri, Medena Noikham, and Sirilata Yotphan. "Persulfate-promoted oxidative C–N bond coupling of quinoxalinones andNH-sulfoximines." Organic & Biomolecular Chemistry 16, no. 15 (2018): 2697–704. http://dx.doi.org/10.1039/c8ob00375k.

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33

Rong, Xiaona, Liujun Jin, Yugui Gu, Guang Liang, and Qinqin Xia. "Transition‐Metal‐Free Radical C−H Methylation of Quinoxalinones with TBHP." Asian Journal of Organic Chemistry 9, no. 2 (2020): 185–88. http://dx.doi.org/10.1002/ajoc.201900758.

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34

Mtiraoui, Hasan, Kevin Renault, Morgane Sanselme, Moncef Msaddek, Pierre-Yves Renard, and Cyrille Sabot. "Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones." Organic & Biomolecular Chemistry 15, no. 14 (2017): 3060–68. http://dx.doi.org/10.1039/c7ob00205j.

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35

Lawrence, David S., Jean E. Copper, and Charles D. Smith. "Structure−Activity Studies of Substituted Quinoxalinones as Multiple-Drug-Resistance Antagonists." Journal of Medicinal Chemistry 44, no. 4 (2001): 594–601. http://dx.doi.org/10.1021/jm000282d.

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36

Dudash, Joseph, Yongzheng Zhang, John B. Moore, et al. "Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors." Bioorganic & Medicinal Chemistry Letters 15, no. 21 (2005): 4790–93. http://dx.doi.org/10.1016/j.bmcl.2005.07.021.

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37

Ji, Yunpeng, Xin Chen, Huan Chen, et al. "Designing of acyl sulphonamide based quinoxalinones as multifunctional aldose reductase inhibitors." Bioorganic & Medicinal Chemistry 27, no. 8 (2019): 1658–69. http://dx.doi.org/10.1016/j.bmc.2019.03.015.

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38

Carta, Antonio, Paolo Sanna, Laura Gherardini, Donatella Usai, and Stefania Zanetti. "Novel functionalized pyrido[2,3-g]quinoxalinones as antibacterial, antifungal and anticancer agents." Il Farmaco 56, no. 12 (2001): 933–38. http://dx.doi.org/10.1016/s0014-827x(01)01161-2.

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39

Ghiaty, Adel. "DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL [1,2,4]TRIAZOLO[4,3-A] QUINOXALINONES." Al-Azhar Journal of Pharmaceutical Sciences 52, no. 2 (2015): 208–18. http://dx.doi.org/10.21608/ajps.2015.12554.

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40

Luo, Xuehong, Etienne Chenard, Peter Martens, Yun-Xing Cheng, and Miroslaw J. Tomaszewski. "ChemInform Abstract: Practical Synthesis of Quinoxalinones via Palladium-Catalyzed Intramolecular N-Arylations." ChemInform 41, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.201050167.

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41

Rueping, Magnus, Francisco Tato, and Fenja R. Schoepke. "The First General, Efficient and Highly Enantioselective Reduction of Quinoxalines and Quinoxalinones." Chemistry - A European Journal 16, no. 9 (2010): 2688–91. http://dx.doi.org/10.1002/chem.200902907.

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42

Hoang, Thanh T., Tuong A. To, Vi T. T. Cao, Anh T. Nguyen, Tung T. Nguyen, and Nam T. S. Phan. "Direct oxidative C H amination of quinoxalinones under copper-organic framework catalysis." Catalysis Communications 101 (November 2017): 20–25. http://dx.doi.org/10.1016/j.catcom.2017.07.012.

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43

Jin, Jianzhong, Jianying Tong, Wenbo Yu, Jun Qiao, and Chao Shen. "Iodobenzene-catalyzed oxidative C H d-alkoxylation of quinoxalinones with deuterated alcohols." Catalysis Communications 141 (June 2020): 106008. http://dx.doi.org/10.1016/j.catcom.2020.106008.

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44

Mbuvi, Harun M., Erik R. Klobukowski, Gina M. Roberts, and L. Keith Woo. "O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources." Journal of Porphyrins and Phthalocyanines 14, no. 03 (2010): 284–92. http://dx.doi.org/10.1142/s1088424610001982.

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Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl , efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give

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45

Mukherjee, Chandrani, Kenneth T. Watanabe, and Edward R. Biehl. "Microwave assisted synthesis of novel imidazo [2,1-b]thiazole derivative attached to quinoxalinones." Tetrahedron Letters 53, no. 45 (2012): 6008–14. http://dx.doi.org/10.1016/j.tetlet.2012.08.093.

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46

Chanda, Kaushik, Jaren Kuo, Chih-Hau Chen, and Chung-Ming Sun. "Enantioselective Synthesis of Benzimidazolyl Quinoxalinones on Soluble Polymer Support Using Focused Microwave Irradiation." Journal of Combinatorial Chemistry 11, no. 2 (2009): 252–60. http://dx.doi.org/10.1021/cc800137p.

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47

Chou, Cheng-Ting, Gorakh S. Yellol, Wong-Jin Chang, Mei-Lian Sun, and Chung-Ming Sun. "Microwave assisted straightforward synthetic method for benzimidazole linked quinoxalinones on soluble polymer support." Tetrahedron 67, no. 11 (2011): 2110–17. http://dx.doi.org/10.1016/j.tet.2011.01.040.

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48

Chen, Bajin, Shengpeng Wang, Jinxing Song, Xiaojun Wang, Bencheng Yu, and Xiaobo Yang. "Direct C-H arylation of quinoxalinones with aryl acylperoxides under catalyst-free condition." Tetrahedron Letters 62 (January 2021): 152681. http://dx.doi.org/10.1016/j.tetlet.2020.152681.

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49

Wang, Fang, Bo-Lun Hu, Lizhi Liu, Hai-Yong Tu, and Xing-Guo Zhang. "One-Pot Synthesis of Quinoxalinones via Tandem Nitrosation/Cyclization of N-Aryl Cyanoacetamides." Journal of Organic Chemistry 82, no. 20 (2017): 11247–52. http://dx.doi.org/10.1021/acs.joc.7b01930.

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50

Qin, Xiangyu, Xin Hao, Hui Han, et al. "Design and Synthesis of Potent and Multifunctional Aldose Reductase Inhibitors Based on Quinoxalinones." Journal of Medicinal Chemistry 58, no. 3 (2015): 1254–67. http://dx.doi.org/10.1021/jm501484b.

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