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Journal articles on the topic 'Iminoquinone'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Dong, Yu, Zhong-Hui Li, Bing He, Hui Jiang, Xiang-Long Chen, Ji-Xian Ye, Qiang Zhou, Long-Sen Gao, Qi-Qi Luo, and Zhi-Chuan Shi. "Silver-Catalyzed One-Pot Biarylamination of Quinones with Arylamines: Access to N-Arylamine-Functionalized p-Iminoquinone Derivatives." Synthesis 54, no. 09 (February 7, 2022): 2242–50. http://dx.doi.org/10.1055/s-0041-1737340.

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AbstractConcise one-pot biarylamination of quinones with arylamines was developed to synthesize N-arylamine-functionalized p-iminoquinones derivatives. The approach employed AgOAc as the catalyst and (NH4)2S2O8 as the oxidant in the presence of 3-chlorophenylboronic acid, giving a series of N-arylamine-functionalized p-iminoquinone derivatives in moderate to good yields whereas reaction in the absence of the 3-chlorophenylboronic acid, gave a series of N-arylamine-functionalized 1,4-naphthoquinone derivatives. This catalytic approach represents a step-economic and convenient strategy for the difunctionalization of quinones.

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2

Bouchard, Luc, Ian Marcotte, Jean Marc Chapuzet, and Jean Lessard. "Electroreduction of 1-methyl 5-nitroindole, 5-nitrobenzofurane, and 5-nitrobenzothiophene in acidic and basic hydroorganic media: Generation and trapping of iminoquinone-type intermediates and electrosynthesis of ring-substituted amino derivatives." Canadian Journal of Chemistry 81, no. 10 (October 1, 2003): 1108–18. http://dx.doi.org/10.1139/v03-149.

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Preparative electrolysis of 1-methyl-5-nitroindole (1b, X = NCH3), 5-nitrobenzofurane (1c, X = O), and 5-nitrobenzothiophene (1d, X = S) at Hg, in acidic hydromethanolic media, leads to the formation of the corresponding 4-substituted amino derivatives 5, which result from the 100% regioselective addition to iminoquinone-type intermediate 4 of methanol or of any other good nucleophile present in the electrolytic solution. In acidic medium, the iminoquinonium intermediates 4b and 4c were trapped in a cycloaddition reaction with cyclopentadiene added to the electrolysis medium. The regiochemistry of the nucleophilic addition is discussed in light of AM1 calculations. Key words: 1-methyl-5-nitroindole, 5-nitrobenzofurane, 5-nitrobenzothiophene, iminoquinone, electrosynthesis.

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3

Klementyeva, Svetlana V., Anton N. Lukoyanov, Mikhail Yu Afonin, Max Mörtel, Anton I. Smolentsev, Pavel A. Abramov, Alyona A. Starikova, Marat M. Khusniyarov, and Sergey N. Konchenko. "Europium and ytterbium complexes with o-iminoquinonato ligands: synthesis, structure, and magnetic behavior." Dalton Transactions 48, no. 10 (2019): 3338–48. http://dx.doi.org/10.1039/c8dt04849e.

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4

Chandrasekar, Selvaraj, and Govidasamy Sekar. "An efficient synthesis of iminoquinones by a chemoselective domino ortho-hydroxylation/oxidation/imidation sequence of 2-aminoaryl ketones." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3053–60. http://dx.doi.org/10.1039/c5ob02659h.

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5

Bamford, Karlee L., Lauren E. Longobardi, Lei Liu, Stefan Grimme, and Douglas W. Stephan. "FLP reduction and hydroboration of phenanthrene o-iminoquinones and α-diimines." Dalton Transactions 46, no. 16 (2017): 5308–19. http://dx.doi.org/10.1039/c7dt01024a.

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Hydrogenation and hydroboration of an N-aryl-phenanthrene-o-iminoquinone and two N,N′-diaryl-phenanthrene α-diimines give a series of derivatives including 1,3,2-oxaza- and diazaboroles and borocyclic radicals.

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6

Kamitanaka, Tohru, Koji Morimoto, Toshifumi Dohi, and Yasuyuki Kita. "Controlled-Coupling of Quinone Monoacetals by New Activation Methods: Regioselective Synthesis of Phenol-Derived Compounds." Synlett 30, no. 10 (March 25, 2019): 1125–43. http://dx.doi.org/10.1055/s-0037-1611735.

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We have studied for a long time the reaction of quinone acetal type compounds, such as quinone monoacetals, quinone O,S-acetals, and iminoquinone monoacetals, and have reported the regioselective introduction of various nucleophiles. Quinone monoacetals show various types of reactivities toward nucleophiles due to their unique structures. In this study, we found that aromatic and alkene nucleophiles can be regioselectively introduced into the α-position of the carbonyl group on quinone monoacetals by specific activation of the acetal moiety. These reactions enabled the metal-free synthesis of highly functionalized aromatic compounds by the regioselective introduction of nucleophiles. In this account, we describe our recent studies of the coupling of quinone monoacetals.1 Introduction2 Regioselective Introduction of Aromatic Nucleophiles into α-Position of Carbonyl2.1 Biaryl Synthesis by Introduction of Aromatic Nucleophiles2.2 Synthesis of Terphenyls and Oligoarenes by Iterative Coupling2.3 Synthesis of Phenol Cross-Coupling Products3 [3+2] Coupling with Alkene Nucleophiles3.1 Development of Efficient [3+2] Coupling3.2 Improvement of Brønsted Acid Promotor4 Synthesis of α-Aryl Carbonyl Compounds Triggered by Silyl Transfer5 Utilization of o-Quinone Monoacetals6 Application to Iminoquinone Monoacetals7 Conclusion

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7

Conboy, Darren, and Fawaz Aldabbagh. "6-Imino-1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1′,2′:1,2]imidazo[4,5-f]benzimidazole-13-one: Synthesis and Cytotoxicity Evaluation." Molbank 2020, no. 1 (March 5, 2020): M1118. http://dx.doi.org/10.3390/m1118.

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The first report of an iminoquinone of imidazo[4,5-f]benzimidazole is described. The 2D-NOESY spectrum of 1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1’,2’:1,2]imidazo[4,5-f]benzimidazol-6-amine was used to confirm the location of the imine moiety at the C-6 position of the title compound. Cytotoxicity data from the National Cancer Institute are included.

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8

Johannissen, Linus O., Nigel S. Scrutton, and Michael J. Sutcliffe. "The enzyme aromatic amine dehydrogenase induces a substrate conformation crucial for promoting vibration that significantly reduces the effective potential energy barrier to proton transfer." Journal of The Royal Society Interface 5, suppl_3 (May 21, 2008): 225–32. http://dx.doi.org/10.1098/rsif.2008.0068.focus.

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The role of promoting vibrations in enzymic reactions involving hydrogen tunnelling is contentious. While models incorporating such promoting vibrations have successfully reproduced and explained experimental observations, it has also been argued that such vibrations are not part of the catalytic effect. In this study, we have employed combined quantum mechanical/molecular mechanical methods with molecular dynamics and potential energy surface calculations to investigate how enzyme and substrate motion affects the energy barrier to proton transfer for the rate-limiting H-transfer step in aromatic amine dehydrogenase (AADH) with tryptamine as substrate. In particular, the conformation of the iminoquinone adduct induced by AADH was found to be essential for a promoting vibration identified previously—this lowers significantly the ‘effective’ potential energy barrier, that is the barrier which remains to be surmounted following collective, thermally equilibrated motion attaining a quantum degenerate state of reactants and products. When the substrate adopts a conformation similar to that in the free iminoquinone, this barrier was found to increase markedly. This is consistent with AADH facilitating the H-transfer event by holding the substrate in a conformation that induces a promoting vibration.

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9

Liu, Liu, Kun Chen, Wen-Zhen Wu, Peng-Fei Wang, Hang-Yu Song, Hongbin Sun, Xiaoan Wen, and Qing-Long Xu. "Organocatalytic Para-Selective Amination of Phenols with Iminoquinone Monoacetals." Organic Letters 19, no. 14 (July 11, 2017): 3823–26. http://dx.doi.org/10.1021/acs.orglett.7b01700.

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10

Ershova, I. V., and A. V. Piskunov. "Complexes of Group III Metals based on o-Iminoquinone Ligands." Russian Journal of Coordination Chemistry 46, no. 3 (March 2020): 154–77. http://dx.doi.org/10.1134/s1070328420030021.

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11

Matson, Ellen M., Sebastian M. Franke, Nickolas H. Anderson, Timothy D. Cook, Phillip E. Fanwick, and Suzanne C. Bart. "Radical Reductive Elimination from Tetrabenzyluranium Mediated by an Iminoquinone Ligand." Organometallics 33, no. 8 (April 7, 2014): 1964–71. http://dx.doi.org/10.1021/om4012104.

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12

Kovacic, Peter, and Ratnasamy Somanathan. "Mechanism of Anesthetic Toxicity: Metabolism, Reactive Oxygen Species, Oxidative Stress, and Electron Transfer." ISRN Anesthesiology 2011 (January 17, 2011): 1–10. http://dx.doi.org/10.5402/2011/402906.

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There is much literature on the toxic effects of anesthetics. This paper deals with both the volatiles and locals. Adverse effects appear to be multifaceted, with the focus on radicals, oxidative stress (OS), and electron transfer (ET). ET functionalities involved are quinone, iminoquinone, conjugated iminium, and nitrone. The non-ET routes involving radicals and OS apparently pertain to haloalkanes and ethers. Beneficial effects of antioxidants, evidently countering OS, are reported. Knowledge at the molecular level should aid in devising strategies to combat the adverse effects.

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13

Xu, Bin, Anjie Ma, Teng Jia, Zhiqiang Hao, Wei Gao, and Ying Mu. "Synthesis and structural characterization of iron complexes bearing N-aryl-phenanthren-o-iminoquinone ligands." Dalton Transactions 45, no. 44 (2016): 17966–73. http://dx.doi.org/10.1039/c6dt03572h.

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Treatments of N-aryl-phenanthren-o-iminoquinone (aryl = 2,6-Me₂C₆H₃ (^MeL); 2,6-ⁱPr₂C₆H₃ (^iPrL)) with iron powder in THF at 75 °C generate complexes [η²L]₂Fe[η¹LH] (1a, L = ^MeL; 1b, L = ^iPrL) in moderate yields.

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14

Mondal, Manas Kumar, and Chandan Mukherjee. "An unprecedented one-step synthesis of octahedral Cu(ii)-bis(iminoquinone) complexes and their reactivity with NaBH4." Dalton Transactions 45, no. 34 (2016): 13532–40. http://dx.doi.org/10.1039/c6dt02443b.

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The non-innocent ligands, H₂L^{AP(o-NO2-OPh)} and H₂L^AP, upon reacting with 2 equivalents of CuCl₂·2H₂O in the presence of Et₃N and air provided the corresponding octahedral Cu(ii)-bis(iminoquinone) complexes (2 and 3) in one-step. The complexes underwent reduction by NaBH₄ in dry CH₃CN and produced H₂ gas.

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15

Meshcheryakova, I. N., O. Yu Trofimova, N. O. Druzhkov, K. I. Pashanova, I. A. Yakushev, P. V. Dorovatovskii, M. N. Khrizanforov, Yu G. Budnikova, R. R. Aisin, and A. V. Piskunov. "Magnesium and Nickel Complexes with Bis(p-iminoquinone) Redox-Active Ligand." Russian Journal of Coordination Chemistry 47, no. 5 (May 2021): 307–18. http://dx.doi.org/10.1134/s1070328421050043.

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Abstract Poorly soluble in the most part of organic solvents dimeric complexes $${\text{M}}{{{\text{g}}}_{{\text{2}}}}{\text{L}}_{2}^{2}$$·4DMF (I) and $${\text{N}}{{{\text{i}}}_{{\text{2}}}}{\text{L}}_{2}^{2}$$·4DMF (II) (L is 4,4'-(1,4-phenylenebis(azanylylidene))bis(3,6-di-tert-butyl-2-hydroxycyclohexa-2,5-dien-1-one dianion)) are synthesized by the reactions of magnesium and nickel acetates with the ditopic redox-active ligand of the hydroxy-para-iminoquinone type in a DMF solution. The molecular and crystal structures of the synthesized compounds are determined by X-ray diffraction analysis (CIF files CCDC nos. 2045665 (I) and 2045666 (II·3DMF)). The thermal stability is studied by thermogravimetry. The redox-active character of the organic bridging ligand in the dimeric complexes $${\text{M}}{{{\text{g}}}_{{\text{2}}}}{\text{L}}_{2}^{2}$$·4DMF and $${\text{N}}{{{\text{i}}}_{{\text{2}}}}{\text{L}}_{2}^{2}$$·4DMF is confirmed by the data of solid-phase electrochemistry.

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16

Ezell, Scharri J., Haibo Li, Hongxia Xu, Xiangrong Zhang, Evrim Gurpinar, Xu Zhang, Elizabeth R. Rayburn, et al. "Preclinical Pharmacology of BA-TPQ, a Novel Synthetic Iminoquinone Anticancer Agent." Marine Drugs 8, no. 7 (July 13, 2010): 2129–41. http://dx.doi.org/10.3390/md8072129.

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17

Mure, Minae, Shinobu Itoh, and Yoshiki Ohshiro. "Preparation and characterization of iminoquinone and aminophenol derivatives of coenzyme PQQ." Tetrahedron Letters 30, no. 49 (January 1989): 6875–78. http://dx.doi.org/10.1016/s0040-4039(01)93377-5.

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18

Abakumov, G. A., V. K. Cherkasov, A. V. Piskunov, I. N. Meshcheryakova, A. V. Maleeva, A. I. Poddel’skii, and G. K. Fukin. "Zinc molecular complexes with sterically hindered o-quinone and o-iminoquinone." Doklady Chemistry 427, no. 1 (July 2009): 168–71. http://dx.doi.org/10.1134/s0012500809070064.

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19

Bochkarev, Mikhail N., Anatoly A. Fagin, Nikolai O. Druzhkov, Vladimir K. Cherkasov, Marina A. Katkova, Georgy K. Fukin, and Yurii A. Kurskii. "Synthesis and characterization of phenanthren-o-iminoquinone complexes of rare earth metals." Journal of Organometallic Chemistry 695, no. 25-26 (December 2010): 2774–80. http://dx.doi.org/10.1016/j.jorganchem.2010.06.024.

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20

Xue, Bing, Wei Wang, Jiang-Jiang Qin, Bhavitavya Nijampatnam, Srinivasan Murugesan, Veronika Kozlovskaya, Ruiwen Zhang, Sadanandan E. Velu, and Eugenia Kharlampieva. "Highly efficient delivery of potent anticancer iminoquinone derivative by multilayer hydrogel cubes." Acta Biomaterialia 58 (August 2017): 386–98. http://dx.doi.org/10.1016/j.actbio.2017.06.004.

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21

Chegerev, Maxim G., Alexandr V. Piskunov, Alyona A. Starikova, Stanislav P. Kubrin, Georgy K. Fukin, Vladimir K. Cherkasov, and Gleb A. Abakumov. "Redox Isomerism in Main-Group Chemistry: Tin Complex with o -Iminoquinone Ligands." European Journal of Inorganic Chemistry 2018, no. 9 (March 2, 2018): 1087–92. http://dx.doi.org/10.1002/ejic.201701361.

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22

Chagas, Manoel P., Josué C. C. Santos, Eduardo B. G. N. Santos, Tiago D. Oliveira, and Mauro Korn. "Exploiting iminoquinone free radical production for thiol based drugs determination in pharmaceutical formulations." Journal of the Brazilian Chemical Society 20, no. 9 (2009): 1646–52. http://dx.doi.org/10.1590/s0103-50532009000900012.

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23

Speier, Gabor, Jozsef Csihony, Anne M. Whalen, and Cortlandt G. Pierpont. "Iminoquinone coordination to copper(I) in the [Cu(PhenoxBQ)(μ-Cl)]2 dimer." Inorganica Chimica Acta 245, no. 1 (April 1996): 1–5. http://dx.doi.org/10.1016/0020-1693(95)04792-1.

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24

Rochford, Jonathan, Ming-Kang Tsai, David J. Szalda, Julie L. Boyer, James T. Muckerman, and Etsuko Fujita. "Oxidation State Characterization of Ruthenium 2−Iminoquinone Complexes through Experimental and Theoretical Studies." Inorganic Chemistry 49, no. 3 (February 2010): 860–69. http://dx.doi.org/10.1021/ic901194k.

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25

Skibo, E. B. "The Discovery of the Pyrrolo[1,2-a]benzimidazole Antitumor Agents - The Design of Selective Antitumor Agents." Current Medicinal Chemistry 3, no. 1 (February 1996): 47–78. http://dx.doi.org/10.2174/092986730301220224163834.

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Abstract: This review presents the design, chemistry, cytotoxicity, and antitumor activity of agents based on the pyrrolo[1,2-a]benzimidazole ring system. The 6-aziridinyl derivatives (PSis) alkylate and cleave DNA upon two electron reduction as a result of phosphate nucleophile-mediated opening of the protonated aziridine ring. The 6-acetamido quinone (APSI) and iminoquinone (imino-APSI) derivatives do not require reductive activation to exert cytotoxicity. The 6-acetamido quinone derivatives act as DNA intercalating agents and inhibit the first step of topoisomerase II mediated DNA relaxation. The PSis were found to exhibit high toxicity in mice with minimal antitumor activity. In contrast, the APSis showed significant increases in life spans of mice as well as activity against tumors distant from the injection site.

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26

Sweeney, Martin, Darren Conboy, Styliana I. Mirallai, and Fawaz Aldabbagh. "Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles." Molecules 26, no. 9 (May 4, 2021): 2684. http://dx.doi.org/10.3390/molecules26092684.

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This review article provides a perspective on the synthesis of alicyclic and heterocyclic ring-fused benzimidazoles, imidazo[4,5-f]benzimidazoles, and imidazo[5,4-f]benzimidazoles. These heterocycles have a plethora of biological activities with the iminoquinone and quinone derivatives displaying potent bioreductive antitumor activity. Synthesis is categorized according to the cyclization reaction and mechanisms are detailed. Nitrobenzene reduction, cyclization of aryl amidines, lactams and isothiocyanates are described. Protocols include condensation, cross-dehydrogenative coupling with transition metal catalysis, annulation onto benzimidazole, often using CuI-catalysis, and radical cyclization with homolytic aromatic substitution. Many oxidative transformations are under metal-free conditions, including using thermal, photochemical, and electrochemical methods. Syntheses of diazole analogues of mitomycin C derivatives are described. Traditional oxidations of o-(cycloamino)anilines using peroxides in acid via the t-amino effect remain popular.

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27

Imamura, Keisuke. "Construction of Multi-Nitrogen-Containing Iminoquinone Skeleton and its Application to Natural Product Synthesis." Journal of Synthetic Organic Chemistry, Japan 64, no. 8 (2006): 867–68. http://dx.doi.org/10.5059/yukigoseikyokaishi.64.867.

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28

Piskunov, A. V., M. G. Chegerev, L. B. Vaganova, and G. K. Fukin. "New paramagnetic tin(IV) complexes based on o-iminoquinone ligands: Synthesis and thermal transformation." Russian Journal of Coordination Chemistry 41, no. 7 (June 24, 2015): 428–35. http://dx.doi.org/10.1134/s1070328415070076.

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29

Fernandes, Luiza, Nathalia Moraes, Fernanda S. Sagrillo, Augusto V. Magalhães, Marcela C. de Moraes, Luciana Romão, Jeffery W. Kelly, Debora Foguel, Neil P. Grimster, and Fernando L. Palhano. "An ortho-Iminoquinone Compound Reacts with Lysine Inhibiting Aggregation while Remodeling Mature Amyloid Fibrils." ACS Chemical Neuroscience 8, no. 8 (May 4, 2017): 1704–12. http://dx.doi.org/10.1021/acschemneuro.7b00017.

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30

Bucher, Götz. "Photochemical Generation of Iminoquinone Methides by 1,4-Hydrogen Migration in Derivatives of o-Tolylnitrene." European Journal of Organic Chemistry 2001, no. 13 (July 2001): 2447–62. http://dx.doi.org/10.1002/1099-0690(200107)2001:13<2447::aid-ejoc2447>3.0.co;2-n.

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31

Piskunov, Alexandr V., Arina V. Maleeva, Irina N. Mescheryakova, and Georgii K. Fukin. "The Reduction of Sterically Hindered o-Quinone and o-Iminoquinone with Gallium and “GaI”." European Journal of Inorganic Chemistry 2012, no. 27 (August 8, 2012): 4318–26. http://dx.doi.org/10.1002/ejic.201200535.

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32

Bucher, Götz, and Hans-Gert Korth. "Photochemistry ofortho-Phenoxymethyl-Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?" Angewandte Chemie International Edition 38, no. 1-2 (January 15, 1999): 212–15. http://dx.doi.org/10.1002/(sici)1521-3773(19990115)38:1/2<212::aid-anie212>3.0.co;2-9.

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33

Wen, Bo, and David J. Moore. "Bioactivation of Glafenine by Human Liver Microsomes and Peroxidases: Identification of Electrophilic Iminoquinone Species and GSH Conjugates." Drug Metabolism and Disposition 39, no. 9 (May 31, 2011): 1511–21. http://dx.doi.org/10.1124/dmd.111.039396.

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34

Chegerev, M. G., and A. V. Piskunov. "Chemistry of Complexes of Group 14 Elements Based on Redox-Active Ligands of the o-Iminoquinone Type." Russian Journal of Coordination Chemistry 44, no. 4 (April 2018): 258–71. http://dx.doi.org/10.1134/s1070328418040036.

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35

Pei, Jiying, Cheng-Chih Hsu, Ruijie Zhang, Yinghui Wang, Kefu Yu, and Guangming Huang. "Unexpected Reduction of Iminoquinone and Quinone Derivatives in Positive Electrospray Ionization Mass Spectrometry and Possible Mechanism Exploration." Journal of The American Society for Mass Spectrometry 28, no. 11 (August 7, 2017): 2454–61. http://dx.doi.org/10.1007/s13361-017-1770-4.

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36

Lazarev, Georgii G., Francisco Lara, Federico Garcia, and Anton Rieker. "Radical pairs during photolysis of an iminoquinone in single crystals of 2,6-di-tert-butyl-4-methylphenol." Chemical Physics Letters 199, no. 1-2 (October 1992): 29–32. http://dx.doi.org/10.1016/0009-2614(92)80044-c.

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37

Hu, Ching-Yao, Yu-Jung Liu, and Wen-Hui Kuan. "pH-Dependent Degradation of Diclofenac by a Tunnel-Structured Manganese Oxide." Water 12, no. 8 (August 5, 2020): 2203. http://dx.doi.org/10.3390/w12082203.

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The mechanism of diclofenac (DIC) degradation by tunnel-structured γ-MnO2, with superior oxidative and catalytic abilities, was determined in terms of solution pH. High-performance liquid chromatography with mass spectroscopy (HPLC–MS) was used to identify intermediates and final products of DIC degradation. DIC can be efficiently oxidized by γ-MnO2 in an acidic medium, and the removal rate decreased significantly under neutral and alkaline conditions. The developed model can successfully fit DIC degradation kinetics and demonstrates electron transfer control under acidic conditions and precursor complex formation control mechanism under neutral to alkaline conditions, in which the pH extent for two mechanisms exactly corresponds to the distribution percentage of ionized species of DIC. We also found surface reactive sites (Srxn), a key parameter in the kinetic model for mechanism determination, to be exactly a function of solution pH and MnO2 dosage. The main products of oxidation with a highly active hydroxylation pathway on the tunnel-structured Mn-oxide are 5-iminoquinone DIC, hydroxyl-DIC, and 2,6-dichloro-N-o-tolylbenzenamine.

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38

Whalen, Anne M., Samaresh Bhattacharya, and Cortlandt G. Pierpont. "Iminoquinone complexes of iron and nickel. Structural, magnetic, and electrochemical properties of complexes containing the phenoxazinolate semiquinone radical." Inorganic Chemistry 33, no. 2 (January 1994): 347–53. http://dx.doi.org/10.1021/ic00080a025.

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39

Druzhkov, N. O., I. N. Meshcheryakova, A. V. Cherkasov, and A. V. Piskunov. "New functionalized ditopic redox-active hydroxy-p-iminoquinone-type ligands and mercury(ii) complexes based on these ligands." Russian Chemical Bulletin 69, no. 1 (January 2020): 49–60. http://dx.doi.org/10.1007/s11172-020-2722-x.

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40

Bucher, Götz. "A Laser Flash Photolysis Study on 2-Azido-N,N-diethylbenzylamine − The Reactivity of Iminoquinone Methides in Solution." European Journal of Organic Chemistry 2001, no. 13 (July 2001): 2463–75. http://dx.doi.org/10.1002/1099-0690(200107)2001:13<2463::aid-ejoc2463>3.0.co;2-6.

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41

Chegerev, Maxim G., Alyona A. Starikova, Alexander V. Piskunov, and Vladimir K. Cherkasov. "Valence Tautomerism in Main-Group Complexes? Computational Modeling of Si, Ge, Sn, and Pb Bischelates witho-Iminoquinone Ligands." European Journal of Inorganic Chemistry 2016, no. 2 (December 7, 2015): 252–58. http://dx.doi.org/10.1002/ejic.201501155.

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42

Smith, Arnold L., Alice L. Erwin, Toni Kline, William C. T. Unrath, Kevin Nelson, Allan Weber, and William N. Howald. "Chloramphenicol Is a Substrate for a Novel Nitroreductase Pathway in Haemophilus influenzae." Antimicrobial Agents and Chemotherapy 51, no. 8 (August 2007): 2820–29. http://dx.doi.org/10.1128/aac.00087-07.

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ABSTRACT The p-nitroaromatic antibiotic chloramphenicol has been used extensively to treat life-threatening infections due to Haemophilus influenzae and Neisseria meningitidis; its mechanism of action is the inhibition of protein synthesis. We found that during incubation with H. influenzae cells and lysates, chloramphenicol is converted to a 4-aminophenyl allylic alcohol that lacks antibacterial activity. The allylic alcohol moiety undergoes facile re-addition of water to restore the 1,3-diol, as well as further dehydration driven by the aromatic amine to form the iminoquinone. Several Neisseria species and most chloramphenicol-susceptible Haemophilus species, but not Escherichia coli or other gram-negative or gram-positive bacteria we examined, were also found to metabolize chloramphenicol. The products of chloramphenicol metabolism by species other than H. influenzae have not yet been characterized. The strains reducing the antibiotic were chloramphenicol susceptible, indicating that the pathway does not appear to mediate chloramphenicol resistance. The role of this novel nitroreductase pathway in the physiology of H. influenzae and Neisseria species is unknown. Further understanding of the H. influenzae chloramphenicol reduction pathway will contribute to our knowledge of the diversity of prokaryotic nitroreductase mechanisms.

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Islam, Imadul, and Edward B. Skibo. "Synthesis and physical studies of azamitosene and iminoazamitosene reductive alkylating agents. Iminoquinone hydrolytic stability, syn/anti isomerization, and electrochemistry." Journal of Organic Chemistry 55, no. 10 (May 1990): 3195–205. http://dx.doi.org/10.1021/jo00297a040.

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Zlotkowski, Katherine, William M. Hewitt, Pengcheng Yan, Heidi R. Bokesch, Megan L. Peach, Marc C. Nicklaus, Barry R. O’Keefe, James B. McMahon, Kirk R. Gustafson, and John S. Schneekloth. "Macrophilone A: Structure Elucidation, Total Synthesis, and Functional Evaluation of a Biologically Active Iminoquinone from the Marine HydroidMacrorhynchia philippina." Organic Letters 19, no. 7 (March 27, 2017): 1726–29. http://dx.doi.org/10.1021/acs.orglett.7b00496.

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Raju, Selvam, Pratheepkumar Annamalai, Pei-Ling Chen, Yi-Hung Liu, and Shih-Ching Chuang. "Iptycenes with an acridinone motif developed through [4+2] cycloaddition of tethered naphthalene and iminoquinone via a radical reaction." Chemical Communications 53, no. 46 (2017): 6247–50. http://dx.doi.org/10.1039/c7cc03030d.

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Bucher, Goetz, and Hans-Gert Korth. "ChemInform Abstract: Photochemistry of ortho-Phenoxymethyl-Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?" ChemInform 30, no. 18 (June 16, 2010): no. http://dx.doi.org/10.1002/chin.199918052.

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Pierdominici-Sottile, Gustavo, Marcelo A. Martí, and Juliana Palma. "The role of residue Thr122 of methylamine dehydrogenase on the proton transfer from the iminoquinone intermediate to residue Asp76." Chemical Physics Letters 456, no. 4-6 (May 2008): 243–46. http://dx.doi.org/10.1016/j.cplett.2008.03.023.

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Piskunov, A. V., I. V. Ershova, M. V. Gulenova, K. I. Pashanova, A. S. Bogomyakov, I. V. Smolyaninov, G. K. Fukin, and V. K. Cherkasov. "Effect of an additional functional group on the structure and properties of copper(II) and nickel(II) o-iminoquinone complexes." Russian Chemical Bulletin 64, no. 3 (March 2015): 642–49. http://dx.doi.org/10.1007/s11172-015-0912-8.

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Wen, Bo, and Mingyan Zhou. "Metabolic activation of the phenothiazine antipsychotics chlorpromazine and thioridazine to electrophilic iminoquinone species in human liver microsomes and recombinant P450s." Chemico-Biological Interactions 181, no. 2 (October 2009): 220–26. http://dx.doi.org/10.1016/j.cbi.2009.05.014.

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Bera, Sachinath, Sandip Mondal, Suvendu Maity, Thomas Weyhermüller, and Prasanta Ghosh. "Radical and Non-Radical States of the [Os(PIQ)] Core (PIQ = 9,10-Phenanthreneiminoquinone): Iminosemiquinone to Iminoquinone Conversion Promoted o-Metalation Reaction." Inorganic Chemistry 55, no. 10 (May 5, 2016): 4746–56. http://dx.doi.org/10.1021/acs.inorgchem.6b00040.

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