Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

David R. Chisholm, Garr-Layy Zhou, Ehmke Pohl, Roy Valentine and Andrew Whiting
Beilstein J. Org. Chem. 2016, 12, 1851–1862. https://doi.org/10.3762/bjoc.12.174

Supporting Information

Supporting information features full synthetic procedures, in situ FTIR data plots, copies of 1H, 13C and 11B NMR spectra, and full crystallographic data including images and CIF files.

Supporting Information File 1: Full synthetic procedures, in situ FTIR data plots, and copies of 1H, 13C and 11B NMR spectra.
Format: PDF Size: 2.7 MB Download
Supporting Information File 2: Crystallographic Information Files of compounds 13, 14, 15b, 19, 29, and 30.
Format: ZIP Size: 2.9 MB Download

Cite the Following Article

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines
David R. Chisholm, Garr-Layy Zhou, Ehmke Pohl, Roy Valentine and Andrew Whiting
Beilstein J. Org. Chem. 2016, 12, 1851–1862. https://doi.org/10.3762/bjoc.12.174

How to Cite

Chisholm, D. R.; Zhou, G.-L.; Pohl, E.; Valentine, R.; Whiting, A. Beilstein J. Org. Chem. 2016, 12, 1851–1862. doi:10.3762/bjoc.12.174

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 129.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • 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
  • 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
  • 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
  • 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
Other Beilstein-Institut Open Science Activities