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Journal articles on the topic 'Quinone Derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Norkov, Sergey V., Anton V. Cherkasov, Andrey S. Shavyrin, Maxim V. Arsenyev, Viacheslav A. Kuropatov, and Vladimir K. Cherkasov. "Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands." Beilstein Journal of Organic Chemistry 17 (January 27, 2021): 273–82. http://dx.doi.org/10.3762/bjoc.17.26.

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The fused 1,3-dithiole spacer seems to be very suitable for the functionalization of sterically hindered o-quinones with additional groups capable of coordination of metal ions and/or possessing a redox activity. An effective method for the synthesis of sterically hindered o-quinones containing 1,3-diketonate, dinitrile and p-quinone-methide functional groups at the periphery of the ligand has been developed. The novel compounds have rigid and conjugated structures and exhibit properties typical of o-quinones. A study of their monoreduced semiquinone derivatives reveal that the spin density is

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2

Vilipic, Jovana, Irena Novakovic, Mario Zlatovic, Miroslava Vujcic, Srdjan Tufegdzic, and Dusan Sladic. "Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA lysozyme." Journal of the Serbian Chemical Society 81, no. 12 (2016): 1345–58. http://dx.doi.org/10.2298/jsc160725101v.

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The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. SDS electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e. existence of interactions between the quinones and CT-DNA. Determination of binding constant by absorption titration indicates weak interactions between quinone derivatives and CT-DNA. The quenching of fluorescence of intercalator ethidium bromide from EB-CT-DNA system and of minor groove binder Hoechst

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3

Li, Jin, Kattesh V. Katti, Ronald G. Cavell, A. Alan Pinkerton, and Herbert Nar. "Synthesis and characterization of phosphinimine-substituted trifluoro- or trichloro-p-benzoquinones and their cationic Rh(I) complexes. The crystal and molecular structure of 3,5,6-trichloro-2-(triphenylphosphinimino)-p-benzoquinone." Canadian Journal of Chemistry 74, no. 11 (1996): 2378–85. http://dx.doi.org/10.1139/v96-265.

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Reaction of tetrafluoro- or tetrachloro-p-benzoquinone with silylated phosphoranimines R2R′P=NSiMe3 (R = Ph, Me) yields very highly colored monosubstituted derivatives of the p-quinone that act as two-electron acceptors showing clean, reversible CV traces. The molar absorptivity values are typical of dyes. These ligands also form chelate complexes with Rh(I) precursors using the quinone oxygen and the imine nitrogen donor sites. One of the quinone derivatives, 3,5,6-trichloro-2-(triphenylphosphinimino)-p-benzoquinone, has been structurally characterized. The iminated quinone shows a normal P=N

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4

Müller, Patrick, Olaf Fuhr, and Manfred Döring. "New Phosphorus-Containing Quinone Derivatives II: Tri- and Tetraphosphorylated Quinone Derivatives." Heteroatom Chemistry 24, no. 4 (2013): 252–62. http://dx.doi.org/10.1002/hc.21089.

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5

Alberti, Angelo, Andrew Hudson, Gian Franco Pedulli, W. Grant McGimpsey, and Jeffrey K. S. Wan. "Photochemical reactions of quinonoid compounds with phosphorus derivatives." Canadian Journal of Chemistry 63, no. 4 (1985): 917–21. http://dx.doi.org/10.1139/v85-152.

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The photoreactions of tetraethylpyrophosphite, tetraphenylbiphosphine, diphenylphosphine oxide, and tetraethylbiphosphine disulphide with five quinones or quinonoid compounds have been studied by esr spectroscopy; [Formula: see text] and [Formula: see text] radicals add to both carbon–carbon and carbon–oxygen double bonds, whilst with [Formula: see text] and [Formula: see text] radicals only the species resulting from addition to a carbonyl group are observed. It is also reported that the photogenerated quinone triplets react with tetraethylpyrophosphite leading to the formation of diethoxypho

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6

Nguyen, Thanh V. "Convenient Access to Hydroquinone and Quinone Derivatives from Cyclobutenedione Units." Australian Journal of Chemistry 63, no. 8 (2010): 1309. http://dx.doi.org/10.1071/ch10189.

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An important synthetic method providing access to a variety of heterocyclic and polycyclic quinones and hydroquinones is described. The key transformation involves the thermal ring expansion of cyclobutenedione derivatives to quinone/hydroquinone units. The synthetic utility and recent applications of this method in natural product synthesis are also discussed.

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7

Sladic, Dusan, Irena Novakovic, Zoran Vujcic, et al. "Protein covalent modification of biologically active quinones." Journal of the Serbian Chemical Society 69, no. 11 (2004): 901–7. http://dx.doi.org/10.2298/jsc0411901s.

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The avarone/avarol quinone/hydroquinone couple shows considerable antitumor activity. In this work, covalent modification of ?-lactoglobulin by avarone and its derivatives as well as by the synthetic steroidal quinone 2,5(10)-estradiene- 1,4,17-trione and its derivatives were studied. The techniques for studying chemical modification of ?-lactoglobulin by quinones were: UV/Vis spectrophotometry, SDS PAGE and isoelectrofocusing. SDS PAGE results suggest that polymerization of the protein occurs. It could be seen that the protein of 18 kD gives the bands of 20 kD, 36 kD, 40 kD, 45 kD, 64 kD and

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8

Yang, Xian, Sergio Garcia, Tobias Janoschka, Dénes Kónya, Martin Hager, and Ulrich Schubert. "Novel, Stable Catholyte for Aqueous Organic Redox Flow Batteries: Symmetric Cell Study of Hydroquinones with High Accessible Capacity." Molecules 26, no. 13 (2021): 3823. http://dx.doi.org/10.3390/molecules26133823.

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Owing to their broad range of redox potential, quinones/hydroquinones can be utilized for energy storage in redox flow batteries. In terms of stability, organic catholytes are more challenging than anolytes. The two-electron transfer feature adds value when building all-quinone flow battery systems. However, the dimerization of quinones/hydroquinones usually makes it difficult to achieve a full two-electron transfer in practical redox flow battery applications. In this work, we designed and synthesized four new hydroquinone derivatives bearing morpholinomethylene and/or methyl groups in differ

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9

Gutiérrez, Isela, Sonia G. Bertolotti, M. A. Biasutti, Arnaldo T. Soltermann, and Norman A. García. "Quinones and hydroxyquinones as generators and quenchers of singlet molecular oxygen." Canadian Journal of Chemistry 75, no. 4 (1997): 423–28. http://dx.doi.org/10.1139/v97-048.

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The role of quinones and hydroxyquinones as sensitizers and as quenchers in Type II photooxygenations has been examined. The second aspect is discussed here, through a systematic study, for the first time in the open literature. Quinonic compounds are excellent generators of O2(1Δg) in aprotic solvents (excluding those quinones possessing substituents in positions adjacent to the carbonyl groups, in the case of anthraquinone derivatives). Benzoquinones, anthraquinones, and hydroxy derivatives are good O2(1Δg) quenchers upon dye-sensitized photoirradiation. The excited oxygen species is deactiv

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10

Son, Eun Jin, Jae Hong Kim, Kayoung Kim, and Chan Beum Park. "Quinone and its derivatives for energy harvesting and storage materials." Journal of Materials Chemistry A 4, no. 29 (2016): 11179–202. http://dx.doi.org/10.1039/c6ta03123d.

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Recent advances in the design of quinone-functionalized hybrid materials are reviewed based on quinone's redox, electrical, optical, and metal chelating/reducing properties to determine these materials' applications in energy harvesting and storage systems.

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11

Müller, Patrick, Yana Bykov, Olaf Walter, and Manfred Döring. "New phosphorus-containing quinone derivatives." Heteroatom Chemistry 23, no. 4 (2012): 383–94. http://dx.doi.org/10.1002/hc.21028.

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12

Wang, Dawei, Xiaoli Yu, Bingyang Ge, Hongyan Miao, and Yuqiang Ding. "Synthesis of Sulfonyl Quinone Derivatives by Rh-Catalyzed Sulfonylation of Quinones." Chinese Journal of Organic Chemistry 35, no. 3 (2015): 676. http://dx.doi.org/10.6023/cjoc201412047.

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13

Becker, K., S. Schwaiger, B. Waltenberger, et al. "Immunomodulatory Effects of Diterpene Quinone Derivatives from the Roots ofHorminum pyrenaicumin Human PBMC." Oxidative Medicine and Cellular Longevity 2018 (2018): 1–10. http://dx.doi.org/10.1155/2018/2980295.

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Several phytochemicals were shown to interfere with redox biology in the human system. Moreover, redox biochemistry is crucially involved in the orchestration of immunological cascades. When screening for immunomodulatory compounds, the two interferon gamma- (IFN-γ-) dependent immunometabolic pathways of tryptophan breakdown via indoleamine 2,3-dioxygenase-1 (IDO-1) and neopterin formation by GTP-cyclohydrolase 1 (GTP-CH-I) represent prominent targets, as IFN-γ-related signaling is strongly sensitive to oxidative triggers. Herein, the analysis of these pathway activities in human peripheral mo

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14

SAITO, Hiromitsu, Akira SATO, Tadashi ASHIZAWA, Makoto MORIMOTO, and Tadashi HIRATA. "Synthesis of quinone derivatives of quinocarcin." CHEMICAL & PHARMACEUTICAL BULLETIN 38, no. 12 (1990): 3202–10. http://dx.doi.org/10.1248/cpb.38.3202.

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15

Yagyu, Eiji, Tetsuya Nishimura, and Motomu Yoshimura. "Photochemical Hole Burning of Quinone Derivatives." Japanese Journal of Applied Physics 31, Part 1, No. 2B (1992): 713–14. http://dx.doi.org/10.1143/jjap.31.713.

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16

Valderrama, Jaime A., Hernari Pcssoa-Mahana, and Ricardo Tapia. "Studies on Quinones. Part 22.' Synthesis of 1-Benzazepine-6,9-Quinone Derivatives." Synthetic Communications 22, no. 4 (1992): 629–40. http://dx.doi.org/10.1080/00397919208019261.

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17

Feng, Zikai, Jason A. Smith, Nuri Gueven, and Joselito P. Quirino. "Metabolic Stability of New Mito-Protective Short-Chain Naphthoquinones." Pharmaceuticals 13, no. 2 (2020): 29. http://dx.doi.org/10.3390/ph13020029.

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Short-chain quinones (SCQs) have been identified as potential drug candidates against mitochondrial dysfunction, which is largely dependent on their reversible redox characteristics of the active quinone core. We recently synthesized a SCQ library of > 148 naphthoquinone derivatives and identified 16 compounds with enhanced cytoprotection compared to the clinically used benzoquinone idebenone. One of the major drawbacks of idebenone is its high metabolic conversion in the liver, which significantly restricts its therapeutic activity. Therefore, this study assessed the metabolic stability of

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18

Ibis, Cemil, Sibel Sahinler Ayla, and Senol Yavuz. "Reactions of quinones with some aryl phenols and synthesis of new quinone derivatives." Synthetic Communications 49, no. 2 (2019): 202–11. http://dx.doi.org/10.1080/00397911.2018.1546403.

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19

Hishmat, O. H., S. S. Mabrouk, A. M. M. Nasef, N. M. A. Shayeb, and S. A. Ismail. "Derivatives of Khellinonequinone and their Aflatoxigenic Activity." Zeitschrift für Naturforschung B 43, no. 3 (1988): 343–46. http://dx.doi.org/10.1515/znb-1988-0318.

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Nitration of khellinone leads to the formation of a small amount of 3-nitrokhellinone and 5-acetyl-6-hydroxybenzofuran-4.7-dione (khellinonequinone) as a main product. The latter compound reacts with primary amines to give the corresponding imino compounds. Reaction of khellinone with o-phenylenediamine involves condensation followed by cyclisation. While on the other hand treating with phenyl hydrazines gives the phenyl hydrazone. The pyrazolobenzofuran derivative was obtained by the action of hydrazine hydrate on khellinonequinone. Finally the reaction with malononitrile leads to the formati

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20

Yang, Ruixia, Yucheng Zhao, Meiyu Jiang, Shengjiao Yan, and Jun Lin. "Simple Synthesis of Ketopiperazine-Substituted Quinone Derivatives." Chinese Journal of Organic Chemistry 36, no. 12 (2016): 2941. http://dx.doi.org/10.6023/cjoc201605025.

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21

Škalamera, Đani, Kata Mlinarić-Majerski, Irena Martin Kleiner, et al. "Photochemical Formation of Anthracene Quinone Methide Derivatives." Journal of Organic Chemistry 82, no. 12 (2017): 6006–21. http://dx.doi.org/10.1021/acs.joc.6b02735.

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22

Zhao, Si-Meng, Bin Kuang, Guang-Zhi Zeng, et al. "Nematicidal quinone derivatives from three Rubia plants." Tetrahedron 74, no. 17 (2018): 2115–20. http://dx.doi.org/10.1016/j.tet.2018.02.065.

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23

Zhang, Yanfei, Ali Qadri, and Joel H. Weiner. "The quinone-binding site ofAcidithiobacillus ferrooxidanssulfide: quinone oxidoreductase controls both sulfide oxidation and quinone reduction." Biochemistry and Cell Biology 94, no. 2 (2016): 159–66. http://dx.doi.org/10.1139/bcb-2015-0097.

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Sulfide:quinone oxidoreductase (SQR) is a peripheral membrane enzyme that catalyzes the oxidation of sulfide and the reduction of ubiquinone. Ubiquinone binds to a conserved hydrophobic domain and shuttles electrons from a noncovalent flavin adenine dinucleotide cofactor to the membrane-bound quinone pool. Utilizing the structure of decylubiquinone bound to Acidithiobacillus ferrooxidans SQR, we combined site-directed mutagenesis and kinetic approaches to analyze quinone binding. SQR can reduce both benzoquinones and naphthoquinones. The alkyl side-chain of ubiquinone derivatives enhances bind

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24

Novakovic, Irena, Zoran Vujcic, Tatjana Bozic, Natasa Bozic, Nenad Milosavic та Dusan Sladic. "Chemical modification of β-lactoglobulin by quinines". Journal of the Serbian Chemical Society 68, № 4-5 (2003): 243–48. http://dx.doi.org/10.2298/jsc0305243n.

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The avarone/avarol quinone/hydroquinone couple, as well as their derivatives show considerable antitumor activity. In this work, covalent modifications of ?-lactoglobulin, isolated from cow milk, by avarone, its model compound 2-tert-butyl-1,4-benzoquinone, and several of their alkylthio derivatives were studied. The techniques applied for assaying the modifications were UV/VIS spectrophotometry, SDS PAGE and isoelectrofocusing. The results of the SDS PAGE suggest that polymerisation of the protein occurs. The shift of the pI of the protein upon modification toward lower values indicates that

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25

Zlatovic, Mario, Dusan Sladic, and Miroslav Gasic. "The kinetics of the reduction of the lipophilic quinone avarone by N-alkyl-1,4-dihydronicotinamides of various lipophilicities." Journal of the Serbian Chemical Society 64, no. 11 (1999): 647–54. http://dx.doi.org/10.2298/jsc9911647z.

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Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium- and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anio

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26

VALDERRAMA, J. A., H. PESSOA-MAHANA, and R. TAPIA. "ChemInform Abstract: Studies on Quinones. Part 22. Synthesis of 1-Benzazepine-6,9-quinone Derivatives." ChemInform 23, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199230184.

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27

Hussong, Rita, Heinrich Heydt, and Manfred Regitz. "Phosphorverbindungen ungewöhnlicher Koordination, 13. Abfangreaktionen von Phenyl-thioxophosphan durch [4+1]-CycIoaddition mit o-Chinonen/ Phosphorus Compounds with Unusual Coordination, 13 [1] Trapping Reactions of Phenyl Thioxophosphane by [4+1] Cycloaddition with o-Quinones." Zeitschrift für Naturforschung B 41, no. 7 (1986): 915–21. http://dx.doi.org/10.1515/znb-1986-0719.

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AbstractPhenyl thioxophosphane (1) - generated by thermal cycloreversion from 7 along with the dihydropyridazine 8 - is trapped by [4+1] cycloaddition with the o-quinones 9a-f by formation of the dioxaphospholsulfides 10a-f. Solvolysis of 10a-c, e and f with m ethanol yields the phenol derivatives 12a-e (in the case of 10b the isomer 12b′ is formed, too). This reaction is reversible (12a-c→10a-c) and accompanied by formation of the isomers 13a-c. The phenanthrene quinone methanide 14 is also suitable for the trapping reaction of 1 (→15→17).

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28

Giles, Robin G. F., Ivan R. Green, Francois J. Oosthuizen, and C. Peter Taylor. "Asymmetric diastereoselective syntheses of the aphid insect pigment derivatives quinone A and quinone A′." Tetrahedron Letters 42, no. 33 (2001): 5753–54. http://dx.doi.org/10.1016/s0040-4039(01)00955-8.

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29

Niu, Zhihui, Huaxi Wu, Yihua Lu, et al. "Orbital-dependent redox potential regulation of quinone derivatives for electrical energy storage." RSC Advances 9, no. 9 (2019): 5164–73. http://dx.doi.org/10.1039/c8ra09377f.

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30

Campanini-Salinas, Javier, Juan Andrades-Lagos, Nicolás Hinojosa, et al. "New Quinone Antibiotics against Methicillin-Resistant S. aureus." Antibiotics 10, no. 6 (2021): 614. http://dx.doi.org/10.3390/antibiotics10060614.

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There is an urgent need for the development of new antibiotics. Here, we describe the inhibitory activity of new quinone compounds against methicillin-resistant Staphylococcus aureus (ATCC® 43300), methicillin-sensitive S. aureus (ATCC® 29213), and two clinical isolates from Chile (ISP-213 and ISP-214). We observed 99.9% reduction in viability within 2 h of exposure without the cultures exhibiting any post-antibiotic effect, which was twice the kinetics to that observed with vancomycin. These clinical isolates did not acquire resistance to these quinone derivatives during the course of our stu

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31

Hermane, Jekaterina, Ilona Bułyszko, Simone Eichner, et al. "New, Non-quinone Fluorogeldanamycin Derivatives Strongly Inhibit Hsp90." ChemBioChem 16, no. 2 (2015): 302–11. http://dx.doi.org/10.1002/cbic.201402375.

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32

Lu, Yu-Hung, Jyun-Jhih Lin, Yu-Jen Wu, Jui-Hsin Su, and Mohamed El-Shazly. "Quinone Derivatives from the Soft Coral Sinularia scabra." Chemistry of Natural Compounds 57, no. 1 (2021): 6–8. http://dx.doi.org/10.1007/s10600-021-03267-4.

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33

Banfield, Scott C., and Michael A. Kerr. "The DielsAlder reactions of quinone imine ketals." Canadian Journal of Chemistry 82, no. 2 (2004): 131–38. http://dx.doi.org/10.1139/v03-188.

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N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth DielsAlder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pressures for cycloadditions while the N-tosyl and N-nosyl derivatives proceed under thermal (ambient pressure) conditions. In all cases the cycloadditions are completely regioselective.Key words: DielsAlder, quinone imine ketal, hyperbaric chemistry.

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34

Elnaggar, Mohamed S., Weaam Ebrahim, Attila Mándi, et al. "Hydroquinone derivatives from the marine-derived fungus Gliomastix sp." RSC Advances 7, no. 49 (2017): 30640–49. http://dx.doi.org/10.1039/c7ra04941b.

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35

Russell, RA, RW Longmore, and RN Warrener. "Anodic-Oxidation Products of 2',5'-Dimethoxyacetanilide Derivatives, and Their Application to the Synthesis of Aminoanthraquinones." Australian Journal of Chemistry 44, no. 12 (1991): 1691. http://dx.doi.org/10.1071/ch9911691.

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Anodic oxidation of simple 2′,5′-dimethoxyacetanilides proceeds under mildly basic conditions to afford either monomeric or dimeric quinone bisacetals, depending on the structure of the substrate. Similarly, the oxidation of linked derivatives of 2′,5′-dimethoxyacetanilides is shown to exhibit a comparable sensitivity, with non-alkylated amides being efficiently converted into bis(quinone bisacetals). The regiospecificity of acetal hydrolysis for both simple and linked quinone bisacetals is shown to be dependent upon the nature of the N-acyl group. The annelation of these hydrolysis products w

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36

Jeremic, Marko, Jelena Dinic, Milica Pesic, et al. "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential." Journal of the Serbian Chemical Society 83, no. 11 (2018): 1193–207. http://dx.doi.org/10.2298/jsc180627062j.

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In this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert-butylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/arylamino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cytotoxic activity of the synthesized derivatives towards multidrug resistant (MDR) human non-small cell lung carcinoma NCI-H460/R cells, their sensitive counterpart NCI-H460 and human normal keratinocytes (HaCaT) was investiga

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37

Shaabani, Ahmad, Shahram Ajabi, Farhad Farrokhzad, and Hamid Reza Bijanzadeh. "[1 + 4]Cycloaddition of Isocyanides with 2-Acetyl-1,4-benzoquinone; a Convenient Synthesis of Isobenzofuran-4,7-quinones." Journal of Chemical Research 23, no. 9 (1999): 582–83. http://dx.doi.org/10.1177/174751989902300932.

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38

Feng, Zikai, Mohammed Sedeeq, Abraham Daniel, et al. "Comparative In Vitro Toxicology of Novel Cytoprotective Short-Chain Naphthoquinones." Pharmaceuticals 13, no. 8 (2020): 184. http://dx.doi.org/10.3390/ph13080184.

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Short-chain quinones (SCQs) have been identified as potential drug candidates against mitochondrial dysfunction, which largely depends on the reversible redox characteristics of the active quinone core. We recently identified 11 naphthoquinone derivatives, 1–11, from a library of SCQs that demonstrated enhanced cytoprotection and improved metabolic stability compared to the clinically used benzoquinone idebenone. Since the toxicity properties of our promising SCQs were unknown, this study developed multiplex methods and generated detailed toxicity profiles from 11 endpoint measurements using t

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39

Tsushima, Mitsuki, Yuji Kimura, Ayumi Kashiwada, and Kazunori Yamada. "Removal of Linear and Branched Alkylphenols with the Combined Use of Polyphenol Oxidase and Chitosan." Polymers 11, no. 6 (2019): 931. http://dx.doi.org/10.3390/polym11060931.

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Removal of linear and branched alkylphenols with different alkyl chain lengths or different branchings (normal, secondary, and tertiary), some of which are suspected as endocrine disrupting chemicals, from an aqueous medium were investigated through quinone oxidation by polyphenol oxidase (PPO) and subsequent quinone adsorption on chitosan beads or powders at pH 7.0 and 40 °C. PPO-catalyzed quinone oxidation increased with an increase in alkyl chain length of the alkylphenols used. Although a higher PPO dose was required for quinone oxidation of branched alkylphenols, they were completely or m

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40

Tomai, Takaaki, Hayate Saito, and Itaru Honma. "High-energy-density electrochemical flow capacitors containing quinone derivatives impregnated in nanoporous carbon beads." Journal of Materials Chemistry A 5, no. 5 (2017): 2188–94. http://dx.doi.org/10.1039/c6ta08733g.

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41

Mayer, Szabolcs, Péter Keglevich, Péter Ábrányi-Balogh, et al. "Attempted Diels-Alder Reactions on Vindoline Derivatives." Periodica Polytechnica Chemical Engineering 61, no. 4 (2017): 258. http://dx.doi.org/10.3311/ppch.11087.

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The Diels-Alder reaction of vindoline and methyl vinyl ketone resulted in a Friedel-Crafts reaction product. In the reaction between the ortho-quinone derivative of vindoline and N-phenylmaleimide, two anomalous products were obtained, a vindoline dimer, and a condensed vindoline derivative.

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42

Giles, Robin G. F. "The Diastereoselective Syntheses of Enantiopure Benzo- and Naphtho-pyrans Related to the Aphid Insect Pigments." Australian Journal of Chemistry 57, no. 4 (2004): 329. http://dx.doi.org/10.1071/ch03286.

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An overview is presented of synthetic endeavours directed towards the assembly of the enantiopure quinone A and quinone A′, natural derivatives of the aphid insect pigments protoaphin-fb and protoaphin-sl. These are achieved through intramolecular diastereoselective cyclization of tethered phenolic lactaldehydes. The conformational implications of the cyclization process are discussed. Model reactions allow the formulation of a more concise, convergent route to these natural derivatives through the corresponding intermolecular reactions, in which the required complementary diastereoselectivity

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43

Ding, Weiwei, та Gang Zhang. "Access to fused π-extended acridone derivatives through a regioselective oxidative demethylation". Organic & Biomolecular Chemistry 19, № 32 (2021): 6985–89. http://dx.doi.org/10.1039/d1ob01249e.

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44

Kobayashi, Kazuhiro. "One-pot Syntheses of Heterocycle-fused Quinone Derivatives Based on Reactions of Quinones with Enamines." Journal of Synthetic Organic Chemistry, Japan 62, no. 8 (2004): 811–20. http://dx.doi.org/10.5059/yukigoseikyokaishi.62.811.

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45

Elsworth, John F., Robin G. F. Giles, Ivan R. Green, Jurgen E. Ramdohr, and Selwyn C. Yorke. "Syntheses of the aphid pigment derivatives quinone A, quinone A′, and deoxyquinone A as racemates." J. Chem. Soc., Perkin Trans. 1, no. 8 (1988): 2469–76. http://dx.doi.org/10.1039/p19880002469.

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Wu, Yang, Guanyu Qiao, Honglei Liu, et al. "Brønsted acid-promoted [3 + 3] cycloaddition of azomethine ylides with quinone monoimine: a practical method towards dihydrobenzoxazine derivatives." RSC Advances 5, no. 102 (2015): 84290–94. http://dx.doi.org/10.1039/c5ra12401h.

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47

Kuckländer, Uwe, and Udo Bastian. "Darstellung und Oxidation von 2-(2,5-Dihydroxy-phenyl)-ethylamin-Derivaten, II / Synthesis and Oxidation of 2-(2,5-Dihydroxyphenyl)-ethylamine Derivatives, II." Zeitschrift für Naturforschung B 42, no. 12 (1987): 1567–77. http://dx.doi.org/10.1515/znb-1987-1214.

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Abstract:

Abstract2,5-Dihydroxyphenylethylamine derivatives 8a,b; 14; 19a,b and 25a,b,c are synthesized and oxidized to indole 9a, indolines 15 and 18a,b as well as 24a,b,c. Quantitative oxidation of hydroquinones yields the 2-(aminoethyl)quinones 30a as free base and 30d-f; 27a,b and the hydrochlorides 28a,b. Quinone 30a is reduced to indoline 29 and acetylated to 3-acylindole 32, transformed by heating to indole 23 and in acetic acid to the dimeric indole 31. 32 is synthesized unequivocally from 33 and 34. The course of the reaction is discussed and the formation of indolines is explained by cyclisati

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48

Gerken, James B., Alexios Stamoulis, Sung-Eun Suh, et al. "Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones." Chemical Communications 56, no. 8 (2020): 1199–202. http://dx.doi.org/10.1039/c9cc08878d.

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Yuan, Fu-Ru, Fei Jiang, Ke-Wei Chen, Guang-Jian Mei, Qiong Wu, and Feng Shi. "Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes." Organic & Biomolecular Chemistry 17, no. 9 (2019): 2361–69. http://dx.doi.org/10.1039/c8ob02979b.

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The first [4 + 2] cyclization of para-quinone methide derivatives with allenes has been established via phosphine catalysis, which afforded a series of chroman derivatives in high yields (up to 97%) and excellent (E/Z)-selectivities (all >95 : 5 E/Z).

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50

Monni, Noemi, Mariangela Oggianu, Suchithra Ashoka Sahadevan, and Maria Laura Mercuri. "Redox Activity as a Powerful Strategy to Tune Magnetic and/or Conducting Properties in Benzoquinone-Based Metal-Organic Frameworks." Magnetochemistry 7, no. 8 (2021): 109. http://dx.doi.org/10.3390/magnetochemistry7080109.

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Multifunctional molecular materials have attracted material scientists for several years as they are promising materials for the future generation of electronic devices. Careful selection of their molecular building blocks allows for the combination and/or even interplay of different physical properties in the same crystal lattice. Incorporation of redox activity in these networks is one of the most appealing and recent synthetic strategies used to enhance magnetic and/or conducting and/or optical properties. Quinone derivatives are excellent redox-active linkers, widely used for various appli

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