Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Scholarly Works

• Deng, Z.; Lv, Y.; Hai, X.; Zhu, Z.; Wang, J.; Wang, K.-H.; Huang, D.; Hu, Y. Visible-Light-Induced Metal-Free Radical Cascade Trifluoromethylation/Cyclization for Synthesis of Trifluoromethyl/Trifluoroethyl Tetrahydroquinolines. The Journal of organic chemistry 2025, 90, 15531–15541. doi:10.1021/acs.joc.5c01452
• Zhang, T.; Nishiura, Y.; Cusumano, A. Q.; Stoltz, B. M. Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Lactams: Enantioselective Construction of All-Carbon Quaternary Stereocenters in Saturated Nitrogen-Containing Heterocycles. Organic letters 2023, 25, 6479–6484. doi:10.1021/acs.orglett.3c02064
• Yu. Rulev, A. Aza‐Michael Reaction: A Decade Later – Is the Research Over?. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300451
• Zhang, L.; Xie, D.; Zhang, S. A Method for the Synthesis of 1,2,3,4‐Tetrahydroquinolines through Reduction of Quinolin‐2(1H)‐ones Promoted by SmI2/H2O/Et3N. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202201063
• Couto, J. L.; Hornink, M. M.; Nascimento, V. R.; Andrade, L. H. Fast Transition Metal‐Free Synthesis of Functionalized Oxindoles and Dihydroquinoline‐2‐ones Under Microwave Irradiation. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200962
• Hudhud, L.; Chisholm, D. R.; Whiting, A.; Steib, A.; Pohóczky, K.; Kecskés, A.; Szőke, É.; Helyes, Z. Synthetic Diphenylacetylene-Based Retinoids Induce DNA Damage in Chinese Hamster Ovary Cells without Altering Viability. Molecules (Basel, Switzerland) 2022, 27, 977. doi:10.3390/molecules27030977
• Kimmel, B. R.; Mrksich, M. Development of an Enzyme-Inhibitor Reaction Using Cellular Retinoic Acid Binding Protein II for One-Pot Megamolecule Assembly. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 17843–17848. doi:10.1002/chem.202103059
• Tiekink, E. R. T. Supramolecular architectures sustained by delocalised C–I⋯π(arene) interactions in molecular crystals and the propensity of their formation. CrystEngComm 2021, 23, 904–928. doi:10.1039/d0ce01677b
• Tomlinson, C. W. E.; Cornish, K. A. S.; Whiting, A.; Pohl, E. Structure-functional relationship of cellular retinoic acid-binding proteins I and II interacting with natural and synthetic ligands. Acta crystallographica. Section D, Structural biology 2021, 77, 164–175. doi:10.1107/s2059798320015247
• de Souza, W. C.; Matsuo, B. T.; Matos, P. M.; Correia, J. T. M.; Santos, M. S.; König, B.; Paixão, M. W. Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 3722–3728. doi:10.1002/chem.202003641
• Chisholm, D. R.; Hughes, J. G.; Blacker, T. S.; Humann, R.; Adams, C.; Callaghan, D.; Pujol, A.; Lembicz, N. K.; Bain, A. J.; Girkin, J. M.; Ambler, C. A.; Whiting, A. Cellular localisation of structurally diverse diphenylacetylene fluorophores. Organic & biomolecular chemistry 2020, 18, 9231–9245. doi:10.1039/d0ob01153c
• Fink, D.; Orth, N.; Ebel, V.; Gogesch, F. S.; Staiger, A.; Linseis, M.; Ivanović-Burmazović, I.; Winter, R. F. Self-Assembled Redox-Active Tetraruthenium Macrocycles with Large Intracyclic Cavities. Organometallics 2020, 39, 1861–1880. doi:10.1021/acs.organomet.0c00116
• Tomlinson, C. W. E.; Whiting, A. The development of methodologies for high-throughput retinoic acid binding assays in drug discovery and beyond. Methods in enzymology 2020, 637, 539–560. doi:10.1016/bs.mie.2020.02.008
• Chisholm, D. R.; Lamb, R.; Pallett, T.; Affleck, V.; Holden, C.; Marrison, J.; O'Toole, P.; Ashton, P. D.; Newling, K.; Steffen, A.; Nelson, A. K.; Mahler, C.; Valentine, R.; Blacker, T. S.; Bain, A. J.; Girkin, J. M.; Marder, T. B.; Whiting, A.; Ambler, C. A. Photoactivated cell-killing involving a low molecular weight, donor–acceptor diphenylacetylene. Chemical science 2019, 10, 4673–4683. doi:10.1039/c9sc00199a
• Muthukrishnan, I.; Sridharan, V.; Menéndez, J. C. Progress in the Chemistry of Tetrahydroquinolines. Chemical reviews 2019, 119, 5057–5191. doi:10.1021/acs.chemrev.8b00567
• Chisholm, D. R.; Tomlinson, C. W. E.; Zhou, G.-L.; Holden, C.; Affleck, V.; Lamb, R.; Newling, K.; Ashton, P. D.; Valentine, R.; Redfern, C. P.; Erostyák, J.; Makkai, G.; Ambler, C. A.; Whiting, A.; Pohl, E. Fluorescent Retinoic Acid Analogues as Probes for Biochemical and Intracellular Characterization of Retinoid Signaling Pathways. ACS chemical biology 2019, 14, 369–377. doi:10.1021/acschembio.8b00916
• de Pablo, J. G.; Chisholm, D. R.; Steffen, A.; Nelson, A. K.; Mahler, C.; Marder, T. B.; Peyman, S. A.; Girkin, J. M.; Ambler, C. A.; Whiting, A.; Evans, S. D. Tandem fluorescence and Raman (fluoRaman) characterisation of a novel photosensitiser in colorectal cancer cell line SW480. The Analyst 2018, 143, 6113–6120. doi:10.1039/c8an01461b
• Tomlinson, C. W. E.; Chisholm, D. R.; Valentine, R.; Whiting, A.; Pohl, E. Novel Fluorescence Competition Assay for Retinoic Acid Binding Proteins. ACS medicinal chemistry letters 2018, 9, 1297–1300. doi:10.1021/acsmedchemlett.8b00420
• Haffez, H.; Chisholm, D. R.; Valentine, R.; Pohl, E.; Redfern, C. P.; Whiting, A. The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors. MedChemComm 2017, 8, 578–592. doi:10.1039/c6md00680a

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