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Journal articles on the topic 'Alkyl-quinolones'

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Published: 25 May 2024

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1

Liu, Huanhuan, Huadan Liu, Enhua Wang, et al. "Hydrogen Bond Assisted Three-Component Tandem Reactions to Access N-Alkyl-4-Quinolones." Molecules 28, no. 5 (2023): 2304. http://dx.doi.org/10.3390/molecules28052304.

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Hydrogen-bonding catalytic reactions have gained great interest. Herein, a hydrogen-bond-assisted three-component tandem reaction for the efficient synthesis of N-alkyl-4-quinolones is described. This novel strategy features the first proof of polyphosphate ester (PPE) as a dual hydrogen-bonding catalyst and the use of readily available starting materials for the preparation of N-alkyl-4-quinolones. The method provides a diversity of N-alkyl-4-quinolones in moderate to good yields. The compound 4h demonstrated good neuroprotective activity against N-methyl-ᴅ-aspartate (NMDA)-induced excitotoxi

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2

Mollova-Sapundzhieva, Yordanka, Plamen Angelov, Danail Georgiev та Pavel Yanev. "Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors". Beilstein Journal of Organic Chemistry 19 (23 листопада 2023): 1804–10. http://dx.doi.org/10.3762/bjoc.19.132.

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β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including natural products of microbial origin such as HHQ and its C5-congener. Two compounds with high activity against S. aureus have been identified among the newly obtained quinolones, with MICs ≤ 3.12 and ≤ 6.25 µg/mL, respectively.

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3

Tang, Jing, and Xian Huang. "Convenient synthesis of 5-(Arylamino(Alkylthio)Methylene)-2,2-Dimethyl-1,3-Dioxane-4,6-Diones and 2-Arylthio-4-Quinolones." Journal of Chemical Research 2003, no. 3 (2003): 140–41. http://dx.doi.org/10.3184/030823403103173264.

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Meldrum's acid reacted with an aryl isothiocynate and alkyl halides to afford the 5-(arylamino(alkylthio)methylene)-5-methylthio-2,2-dimethyl-1,3-dioxane-4,6-diones and the compounds underwent thermal cyclization to give the 4-2-arylthio-4(1 H)-quinolones

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4

Bezuglyi, P. A., I. V. Ukrainets, V. I. Treskach, and A. V. Turov. "4-Hydroxy-2-quinolones. 1. Efficient method for obtaining 3-alkyl-4-hydroxy-2-quinolones." Chemistry of Heterocyclic Compounds 27, no. 11 (1991): 1237–38. http://dx.doi.org/10.1007/bf00471752.

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5

Saalim, Muhammad, Jessica Villegas-Moreno, and Benjamin R. Clark. "Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties." Molecules 25, no. 23 (2020): 5689. http://dx.doi.org/10.3390/molecules25235689.

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The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the Pseudomonas and Burkholderia genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from Pseudomonas aeruginosa. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in Pseudom

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6

Vrla, Geoffrey D., Mark Esposito, Chen Zhang, Yibin Kang, Mohammad R. Seyedsayamdost, and Zemer Gitai. "Cytotoxic alkyl-quinolones mediate surface-induced virulence in Pseudomonas aeruginosa." PLOS Pathogens 16, no. 9 (2020): e1008867. http://dx.doi.org/10.1371/journal.ppat.1008867.

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7

BEZUGLYI, P. A., I. V. UKRAINETS, V. I. TRESKATCH, and A. V. TUROV. "ChemInform Abstract: 4-Hydroxy-2-quinolones. Part 1. Effective Preparation of 3-Alkyl-4- hydroxy-2-quinolones." ChemInform 24, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199337226.

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8

Chen, Bang-chi, Xian Huang, and Jin Wang. "A Versatile Synthesis of 2-Alkyl and 2-Aryl 4-Quinolones." Synthesis 1987, no. 05 (1987): 482–83. http://dx.doi.org/10.1055/s-1987-33427.

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9

Gupta, Rashmi, and Martin Schuster. "Quorum sensing modulates colony morphology through alkyl quinolones in Pseudomonas aeruginosa." BMC Microbiology 12, no. 1 (2012): 30. http://dx.doi.org/10.1186/1471-2180-12-30.

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10

Michalet, S., P. M. Allard, C. Commun, et al. "ePS6.03 Alkyl-Quinolones derivatives could predict Pseudomonas infection chronicity in cystic fibrosis." Journal of Cystic Fibrosis 19 (June 2020): S52—S53. http://dx.doi.org/10.1016/s1569-1993(20)30331-3.

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11

Al-Qawasmeh, Raed, Jalal Zahra, Monther Khanfar, Yusuf AL-Hiari, Mustafa El-Abadelah, and Wolfgang Voelter. "A Convenient Synthesis of 1-Alkyl-7-chloro-6-fluoro-3-nitro-4-quinolones." Letters in Organic Chemistry 6, no. 6 (2009): 511–14. http://dx.doi.org/10.2174/157017809789124812.

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12

Song, Yoon Ju, Jin Sun Choi, and Jae In Lee. "An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones from 2-Halobenzoic Acids." Bulletin of the Korean Chemical Society 34, no. 10 (2013): 3117–20. http://dx.doi.org/10.5012/bkcs.2013.34.10.3117.

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13

Dubern, Jean-Frédéric, and Stephen P. Diggle. "Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species." Molecular BioSystems 4, no. 9 (2008): 882. http://dx.doi.org/10.1039/b803796p.

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14

Niewerth, Heiko, Klaus Bergander, Siri Ram Chhabra, Paul Williams, and Susanne Fetzner. "Synthesis and biotransformation of 2-alkyl-4(1H)-quinolones by recombinant Pseudomonas putida KT2440." Applied Microbiology and Biotechnology 91, no. 5 (2011): 1399–408. http://dx.doi.org/10.1007/s00253-011-3378-0.

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15

Li, Dandan, Naoya Oku, Atsumi Hasada, Masafumi Shimizu, and Yasuhiro Igarashi. "Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp." Beilstein Journal of Organic Chemistry 14 (June 14, 2018): 1446–51. http://dx.doi.org/10.3762/bjoc.14.122.

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Exploration of rhizobacteria of the genus Burkholderia as an under-tapped resource of bioactive molecules resulted in the isolation of two new antimicrobial 2-alkyl-4-quinolones. (E)-2-(Hept-2-en-1-yl)quinolin-4(1H)-one (1) and (E)-2-(non-2-en-1-yl)quinolin-4(1H)-one (3) were isolated from the culture broth of strain MBAF1239 together with four known alkylquinolones (2 and 4–6), pyrrolnitrin (7), and BN-227 (8). The structures of 1 and 3 were unambiguously characterized using NMR spectroscopy and mass spectrometry. Compounds 1–8 inhibited the growth of the marine bacterium Tenacibaculum mariti

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16

Ritzmann, Niklas H., Almuth Mährlein, Simon Ernst, Ulrich Hennecke, Steffen L. Drees, and Susanne Fetzner. "Bromination of alkyl quinolones by Microbulbifer sp. HZ11, a marine Gammaproteobacterium, modulates their antibacterial activity." Environmental Microbiology 21, no. 7 (2019): 2595–609. http://dx.doi.org/10.1111/1462-2920.14654.

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17

Ukrainets, I. V., S. G. Taran, O. A. Evtifeeva, et al. "4-Hydroxy-2-quinolones 19. A new synthesis of 3-Alkyl-2-oxo-4-hydroxyquinolines." Chemistry of Heterocyclic Compounds 30, no. 5 (1994): 591–95. http://dx.doi.org/10.1007/bf01169841.

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18

Sáenz, Fabián E., Alexis N. LaCrue, R. Matthew Cross, et al. "4-(1H)-Quinolones and 1,2,3,4-Tetrahydroacridin-9(10H)-Ones Prevent the Transmission of Plasmodium falciparum to Anopheles freeborni." Antimicrobial Agents and Chemotherapy 57, no. 12 (2013): 6187–95. http://dx.doi.org/10.1128/aac.00492-13.

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ABSTRACTMalaria kills approximately 1 million people a year, mainly in sub-Saharan Africa. Essential steps in the life cycle of the parasite are the development of gametocytes, as well as the formation of oocysts and sporozoites, in theAnophelesmosquito vector. Preventing transmission of malaria through the mosquito is necessary for the control of the disease; nevertheless, the vast majority of drugs in use act primarily against the blood stages. The study described herein focuses on the assessment of the transmission-blocking activities of potent antierythrocytic stage agents derived from the

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19

Barr, H., A. Fogarty, N. Halliday, et al. "P92 Systemic alkyl quinolones as novel biomarkers for pulmonary exacerbations in cystic fibrosis: a validation study." Thorax 71, Suppl 3 (2016): A133.2—A134. http://dx.doi.org/10.1136/thoraxjnl-2016-209333.235.

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20

Xu, Bin, Jun Shao, Xiaomei Huang, Xiaohu Hong, and Bingxin Liu. "Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation." Synthesis 44, no. 12 (2012): 1798–805. http://dx.doi.org/10.1055/s-0031-1290775.

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21

Li, Jianye, Weiwei Sun, Muhammad Saalim, Guixiang Wei, Diana A. Zaleta-Pinet, and Benjamin R. Clark. "Isolation of 2-Alkyl-4-quinolones with Unusual Side Chains from a Chinese Pseudomonas aeruginosa Isolate." Journal of Natural Products 83, no. 7 (2020): 2294–98. http://dx.doi.org/10.1021/acs.jnatprod.0c00026.

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22

Legendre, Claire, F. Jerry Reen, Marlies J. Mooij, Gerard P. McGlacken, Claire Adams та Fergal O'Gara. "Pseudomonas aeruginosa Alkyl Quinolones Repress Hypoxia-Inducible Factor 1 (HIF-1) Signaling through HIF-1α Degradation". Infection and Immunity 80, № 11 (2012): 3985–92. http://dx.doi.org/10.1128/iai.00554-12.

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ABSTRACTThe transcription factor hypoxia-inducible factor 1 (HIF-1) has recently emerged to be a crucial regulator of the immune response following pathogen perception, including the response to the important human pathogenPseudomonas aeruginosa. However, as mechanisms involved in HIF-1 activation by bacterial pathogens are not fully characterized, understanding how bacteria and bacterial compounds impact on HIF-1α stabilization remains a major challenge. In this context, we have focused on the effect of secreted factors ofP. aeruginosaon HIF-1 regulation. Surprisingly, we found thatP. aerugin

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23

Pistorius, Dominik, Angelika Ullrich, Simon Lucas, Rolf W. Hartmann, Uli Kazmaier, and Rolf Müller. "Biosynthesis of 2-Alkyl-4(1H)-Quinolones in Pseudomonas aeruginosa: Potential for Therapeutic Interference with Pathogenicity." ChemBioChem 12, no. 6 (2011): 850–53. http://dx.doi.org/10.1002/cbic.201100014.

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24

Shui, Hongling, Yuhong Zhong, Renshi Luo, et al. "Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities." Beilstein Journal of Organic Chemistry 18 (October 27, 2022): 1507–17. http://dx.doi.org/10.3762/bjoc.18.159.

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The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions, wide range of substrates, and environmental friendliness which conforms to the principles of green chemistry. Furthermore, a gram-scale experiment with low catalyst load

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25

Barr, Helen L., Nigel Halliday, David A. Barrett, et al. "Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study." Journal of Cystic Fibrosis 16, no. 2 (2017): 230–38. http://dx.doi.org/10.1016/j.jcf.2016.10.005.

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26

Song, Yoon Ju, Jin Sun Choi, and Jae In Lee. "ChemInform Abstract: An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones (VII) from 2-Halobenzoic Acids." ChemInform 45, no. 9 (2014): no. http://dx.doi.org/10.1002/chin.201409173.

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27

Wube, Abraham, Juan-David Guzman, Antje Hüfner, et al. "Synthesis and Antibacterial Evaluation of a New Series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones." Molecules 17, no. 7 (2012): 8217–40. http://dx.doi.org/10.3390/molecules17078217.

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28

Shao, Jun, Xiaomei Huang, Xiaohu Hong, Bingxin Liu, and Bin Xu. "ChemInform Abstract: Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation." ChemInform 43, no. 41 (2012): no. http://dx.doi.org/10.1002/chin.201241156.

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29

Rampioni, Giordano, Marilena Falcone, Stephan Heeb, et al. "Unravelling the Genome-Wide Contributions of Specific 2-Alkyl-4-Quinolones and PqsE to Quorum Sensing in Pseudomonas aeruginosa." PLOS Pathogens 12, no. 11 (2016): e1006029. http://dx.doi.org/10.1371/journal.ppat.1006029.

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30

Lin, San San, Stefan Kerscher, Ahmad Saleh, Ulrich Brandt, Uwe Groß, and Wolfgang Bohne. "The Toxoplasma gondii type-II NADH dehydrogenase TgNDH2-I is inhibited by 1-hydroxy-2-alkyl-4(1H)quinolones." Biochimica et Biophysica Acta (BBA) - Bioenergetics 1777, no. 11 (2008): 1455–62. http://dx.doi.org/10.1016/j.bbabio.2008.08.006.

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31

Barr, H. L., N. Halliday, D. A. Barrett, et al. "Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study; response to comments." Journal of Cystic Fibrosis 16, no. 6 (2017): e21. http://dx.doi.org/10.1016/j.jcf.2017.09.008.

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32

Ayubi, Erfan, Jamal Hallajzadeh, and Saeid Safiri. "Comment on data sparsity - Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study." Journal of Cystic Fibrosis 16, no. 6 (2017): e19-e20. http://dx.doi.org/10.1016/j.jcf.2017.07.012.

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33

Ukrainets, L. V., O. V. Gorokhova, S. G. Taran, et al. "4-hydroxy-2-quinolones. 22.* Synthesis and biological properties of 1-alkyl(aryl)-2-oxo-3-carbethoxy-4-hydroxyquinolines and their derivatives." Chemistry of Heterocyclic Compounds 30, no. 7 (1994): 829–36. http://dx.doi.org/10.1007/bf01169641.

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34

Seppänen, Otto, Mikko Muuronen, and Juho Helaja. "Gold-Catalyzed Conversion of Aryl- and Alkyl-Substituted 1-(o-Aminophenyl)-2-propyn-1-ones to the Corresponding 2-Substituted 4-Quinolones." European Journal of Organic Chemistry 2014, no. 19 (2014): 4044–52. http://dx.doi.org/10.1002/ejoc.201402224.

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35

Kilani-Feki, Olfa, Gérald Culioli, Annick Ortalo-Magné, Nabil Zouari, Yves Blache, and Samir Jaoua. "Environmental Burkholderia cepacia Strain Cs5 Acting by Two Analogous Alkyl-Quinolones and a Didecyl-Phthalate Against a Broad Spectrum of Phytopathogens Fungi." Current Microbiology 62, no. 5 (2011): 1490–95. http://dx.doi.org/10.1007/s00284-011-9892-6.

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36

Sciscenko, Iván, Paula García-Negueroles, Ana María Amat, et al. "Use of Fluorescence Spectroscopy and Chemometrics to Visualise Fluoroquinolones Photodegradation Major Trends: A Confirmation Study with Mass Spectrometry." Molecules 28, no. 2 (2023): 777. http://dx.doi.org/10.3390/molecules28020777.

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In this work, we employed EEM-PARAFAC (fluorescence excitation-emission matrices-parallel factor analysis) as a low-cost tool to study the oxidation pathways of (fluoro)quinolones. Amounts of 12.5 μM of enrofloxacin (ENR), ciprofloxacin (CIP), ofloxacin (OFL), oxolinic acid (OA), and flumequine (FLU), as individual solutions, were irradiated under UVA light. A 5-component PARAFAC model was obtained, four of them related to the parent pollutants, named as ENR-like (including CIP), OFL-like, OA-like, and FLU-like, and an additional one related to photoproducts, called ENRox-like (with an emissio

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37

Ukrainets, I. V., N. L. Bereznyakova, V. A. Parshikov, and O. V. Gorokhova. "4-Hydroxy-2-quinolones 150*. Efficient synthesis, structure, and biological activities of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides." Chemistry of Heterocyclic Compounds 44, no. 12 (2008): 1493–99. http://dx.doi.org/10.1007/s10593-009-0209-7.

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38

Dow, Lachlan. "How Do Quorum-Sensing Signals Mediate Algae–Bacteria Interactions?" Microorganisms 9, no. 7 (2021): 1391. http://dx.doi.org/10.3390/microorganisms9071391.

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Quorum sensing (QS) describes a process by which bacteria can sense the local cell density of their own species, thus enabling them to coordinate gene expression and physiological processes on a community-wide scale. Small molecules called autoinducers or QS signals, which act as intraspecies signals, mediate quorum sensing. As our knowledge of QS has progressed, so too has our understanding of the structural diversity of QS signals, along with the diversity of bacteria conducting QS and the range of ecosystems in which QS takes place. It is now also clear that QS signals are more than just in

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39

Seppaenen, Otto, Mikko Muuronen, and Juho Helaja. "ChemInform Abstract: Gold-Catalyzed Conversion of Aryl- and Alkyl-Substituted 1-(o-Aminophenyl)-2-propyn-1-ones to the Corresponding 2-Substituted 4-Quinolones." ChemInform 46, no. 8 (2015): no. http://dx.doi.org/10.1002/chin.201508224.

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40

Ukrainets, I. V., N. L. Bereznyakova, A. A. Davidenko, and S. V. Slobodzian. "4-Hydroxy-2-quinolones. 167*. Study of the reaction of ethyl 1-alkyl-substituted 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylates with phosphorus oxychloride." Chemistry of Heterocyclic Compounds 45, no. 8 (2009): 952–56. http://dx.doi.org/10.1007/s10593-009-0367-7.

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41

Depke, Tobias, Janne Gesine Thöming, Adrian Kordes, Susanne Häussler, and Mark Brönstrup. "Untargeted LC-MS Metabolomics Differentiates Between Virulent and Avirulent Clinical Strains of Pseudomonas aeruginosa." Biomolecules 10, no. 7 (2020): 1041. http://dx.doi.org/10.3390/biom10071041.

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Pseudomonas aeruginosa is a facultative pathogen that can cause, inter alia, acute or chronic pneumonia in predisposed individuals. The gram-negative bacterium displays considerable genomic and phenotypic diversity that is also shaped by small molecule secondary metabolites. The discrimination of virulence phenotypes is highly relevant to the diagnosis and prognosis of P. aeruginosa infections. In order to discover small molecule metabolites that distinguish different virulence phenotypes of P. aeruginosa, 35 clinical strains were cultivated under standard conditions, characterized in terms of

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42

Singh, Shweta, Sharanya Nerella, Srihari Pabbaraja, and Goverdhan Mehta. "Access to 2-Alkyl/Aryl-4-(1H)-Quinolones via Orthogonal “NH3” Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F." Organic Letters 22, no. 4 (2020): 1575–79. http://dx.doi.org/10.1021/acs.orglett.0c00172.

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43

Ukrainets, I. V., I. A. Tugaibei, N. L. Bereznyakova, V. N. Kravchenko, and A. V. Turov. "4-Hydroxy-2-quinolones 144. Alkyl-, arylalkyl-, and arylamides of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and their diuretic properties." Chemistry of Heterocyclic Compounds 44, no. 5 (2008): 565–75. http://dx.doi.org/10.1007/s10593-008-0076-7.

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44

UKRAINETS, I. V., O. V. GOROKHOVA, S. G. TARAN, et al. "ChemInform Abstract: 4-Hydroxy-2-quinolones. Part 22. Synthesis and Biological Properties of 1-Alkyl(aryl)-2-oxo-3-carboethoxy-4-hydroxy-quinolines and Their Derivatives." ChemInform 26, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199518153.

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45

Nguyen, Angela T., Jace W. Jones, Max A. Ruge, Maureen A. Kane, and Amanda G. Oglesby-Sherrouse. "Iron Depletion Enhances Production of Antimicrobials by Pseudomonas aeruginosa." Journal of Bacteriology 197, no. 14 (2015): 2265–75. http://dx.doi.org/10.1128/jb.00072-15.

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ABSTRACTCystic fibrosis (CF) is a heritable disease characterized by chronic, polymicrobial lung infections. WhileStaphylococcus aureusis the dominant lung pathogen in young CF patients,Pseudomonas aeruginosabecomes predominant by adulthood.P. aeruginosaproduces a variety of antimicrobials that likely contribute to this shift in microbial populations. In particular, secretion of 2-alkyl-4(1H)-quinolones (AQs) contributes to lysis ofS. aureusin coculture, providing an iron source toP. aeruginosabothin vitroandin vivo. We previously showed that production of one such AQ, thePseudomonasquinolone

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46

Brewer, Luke K., Jace W. Jones, Catherine B. Blackwood, Mariette Barbier, Amanda Oglesby-Sherrouse, and Maureen A. Kane. "Development and bioanalytical method validation of an LC-MS/MS assay for simultaneous quantitation of 2-alkyl-4(1H)-quinolones for application in bacterial cell culture and lung tissue." Analytical and Bioanalytical Chemistry 412, no. 7 (2020): 1521–34. http://dx.doi.org/10.1007/s00216-019-02374-0.

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47

Ukrainets, I. V., L. V. Sidorenko, A. A. Davidenko, and A. K. Yarosh. "4-Hydroxy-2-quinolones. 174.* Hydrochlorides of [(alkylamino)alkyl]amides of 1-allyl- 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydro- quinoline-3-carboxylic acid – a new class of opioid receptor antagonists." Chemistry of Heterocyclic Compounds 46, no. 4 (2010): 445–51. http://dx.doi.org/10.1007/s10593-010-0529-7.

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48

Ukrainets, I. V., L. V. Sidorenko, A. A. Davidenko, and A. K. Yarosh. "ChemInform Abstract: 4-Hydroxy-2-quinolones. Part 174. Hydrochlorides of [(Alkylamino)alkyl]amides of 1-Allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid - A New Class of Opiod Receptor Antagonists." ChemInform 42, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.201104152.

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49

Huang, Bin, Yaqiu Long, Li-Rui Song, He Li, Shen-Feng Wang, and Jian-Ping Lin. "Metal-free Hypervalent Iodine-promoted Tandem Carbonyl Migration and Unactivated C(Ph)-C(Alkyl) Bond Cleavage for Quinolone Scaffold Synthesis." Chemical Communications, 2022. http://dx.doi.org/10.1039/d2cc02245a.

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An unexpected iodine(III)-mediated C(sp3)-C(sp2) bond cleavage of 3-(methylamino)-2-(2-substitutedbenzoyl)acrylates for efficient synthesis of privileged scaffold 4-quinolones was described. Notably, a wide range of alkyl groups (e.g. methyl, tert-butyl or alkyl chain)...

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50

Park, Cheol-Min, Jaehee Bae, and Jiyoung Chae. "Synthesis of 2‐Quinolones based on Visible Light‐Catalyzed Annulation of Diazo compounds." Advanced Synthesis & Catalysis, February 7, 2024. http://dx.doi.org/10.1002/adsc.202301220.

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Abstract:

Herein, we report a photocatalytic method for the synthesis of 2‐quinolones under mild conditions by employing α‐diazo acetamide as substrates. The use of Eosin Y as a photocatalyst allows an economical and environmentally benign synthetic method. The process involves the generation of radicals from diazo compounds promoted by a visible‐light‐induced proton‐coupled electron transfer (PCET) mechanism. The method demonstrates a broad substrate scope to provide various aryl‐ and alkyl‐substituted 2‐quinolones. To support the proposed mechanism, a series of mechanistic experiments were conducted.

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