263
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis of 9-Phenanthrols through a Sequential Ligand-Free Suzuki/Intramolecular Friedel-Crafts Reaction and Their Cytotoxic Activity

, , , &
Pages 1835-1848 | Received 17 Jun 2019, Accepted 28 Nov 2019, Published online: 20 Jan 2020

References

  • A. Kovács, A. Vasas, and J. Hohmann, “Natural Phenanthrenes and Their Biological Activity,” Phytochemistry 69, no. 5 (2008): 1084–110.
  • B. Réthy, A. Kovács, I. Zupkó, P. Forgo, A. Vasas, G. Falkay, and J. Hohmann, “Cytotoxic Phenanthrenes from the Rhizomes of Tamus Communis,” Planta Medica 72, no. 08 (2006): 767–70.
  • S. Estrada, J. J. López-Guerrero, R. Villalobos-Molina, and R. Mata, “Spasmolytic Stilbenoids from Maxillaria Densa,” Fitoterapia 75, no. 7–8 (2004): 690–5.
  • J.-M. Fu, M. J. Sharp, and V. Snieckus, “The Directed Ortho Metalation Connection to Aryl-Aryl Cross Coupling.A General Regiospecific Synthesis of Phenanthrols,” Tetrahedron Letters 29, no. 43 (1988): 5459–62.
  • J.-M. Fu, and V. Snieckus, “The Directed Ortho Metalation – Palladium Catalyzed Cross Coupling Connection. A General Regiospecific Route to 9-Phenanthrols and Phenanthrenes. Exploratory Further Metalation,” Canadian Journal of Chemistry 78, no. 6 (2000): 905–19.
  • K. B. Jørgensen, T. Rantanen, T. Dörfler, and V. Snieckus, “Directed Netalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-Phenanthrenes,” The Journal of Organic Chemistry 80, no. 19 (2015): 9410–24.
  • For a similar procedure, also see: Y. Huang, G. H. Chan, and S. Chiba, “Amide-Directed C − H Sodiation by a Sodium Hydride/Iodide Composite,” Angewandte Chemie International Edition 56, no. 23 (2017): 6544–7.
  • J. F. Guastavino, and R. A. Rossi, “Synthesis of Benzo-Fused Heterocycles by Intramolecular α-Arylation of Ketone Enolate Anions,” The Journal of Organic Chemistry 77, no. 1 (2012): 460–72.
  • H. B. Ling, Z. S. Chen, F. Yang, B. Xu, J. M. Gao, and K. G. Ji, “Gold-Catalyzed Oxidation Terminal Alkyne: An Approach to Synthesize Substituted Dihydronaphthalen-2(1H)‐Ones and Phenanthrenols,” The Journal of Organic Chemistry 82, no. 13 (2017): 7070–6.
  • S. Lin, and T. You, “An Efficient One-Pot Approach to Phenanthrene Derivatives Using a Catalyzed Tandem Ullmann-Pinacol Coupling Reaction,” Tetrahedron 64, no. 42 (2008): 9906–10.
  • Y. Xia, P. Qu, Z. Liu, Z. Ge, Q. Xiao, Y. Zhang, and J. Wang, “Catalyst-Free Intramolecular Formal Carbon Insertion into σ-C-C Bonds: A New Approach toward Phenanthrols and Naphthols,” Angewandte Chemie International Edition 52, no. 9 (2013): 2543–6.
  • A. A. Leon, G. Daub, and I. R. Silverman, “Methanesulfonic Acid. A Useful Cyclizing Acidic Reagent,” The Journal of Organic Chemistry 49, no. 23 (1984): 4544–5.
  • A. Wu, D. Xu, D. Lu, T. M. Penning, I. A. Blair, and R. G. Harvey, “Synthesis of 13C4-Labelled Oxidized Metabolites of the Carcinogenic Polycyclic Aromatic Hydrocarbon Benzo[a]Pyrene,” Tetrahedron 68, no. 35 (2012): 7217–33.
  • D. Tgetford, and A. P. Chorlton, “Investigation of Vat Dyes as Potential High Performance Pigments,” Dyes and Pigments 61, (2004): 49–62.
  • W. M. Seganish, and P. DeShong, “Application of Aryl Siloxane Cross-Coupling to the Synthesis of Allocol Chicinoids,” Organic Letters 8, no. 18 (2006): 3951–4.
  • A. K. Sharma, S. Amin, and S. Kumar, “An Abbreviated Synthesis of 7,12-Dimethylbenz[a]Anthracene and Benzo[c]Chrysene Metabolites Using the Suzuki Reaction,” Polycyclic Aromatic Compounds 22, no. 3–4 (2002): 277–88.
  • For an example of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) promoted Friedel − Crafts acylation reaction, see: H. F. Motiwala, R. H. Vekariya, and J. Aubé, “Intramolecular Friedel − Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-Propanol,” Organic Letters 17, no. 21 (2015): 5484–7.
  • G. Lu, R. Franzén, Q. Zhang, and Y. Xu, “Palladium Charcoal-Catalyzed, Ligandless Suzuki Reaction by Using Tetraarylborates in Water,” Tetrahedron Letters 46, no. 24 (2005): 4255–9.
  • T. Kylmälä, J. Tois, Y. Xu, and R. Franzén, “One Step Synthesis of Diflunisal Using a Pd-Diamine Complex,” Open Chemistry 7, (2009): 818–26.
  • R. R. Nagawade, and B. Shinde, “Synthesis and anti-Bacterial Activity of New Series of 4-(Substituted Biphenyl-4-yl)-6-Methyl-2-Oxo/Thioxo-1,2,3,4-Tetrahydro-Pyrimidine-5-Carboxylic Acid Ethyl Ester,” Journal of Heterocyclic Chemistry 47, (2010): 33–9.
  • E. Capparelli, L. Zinzi, M. Cantore, M. Contino, M. G. Perrone, G. Luurtsema, F. Berardi, R. Perrone, and N. A. Colabufo, “SAR Studies on Tetrahydroisoquinoline Derivatives: The Role of Flexibility and Bioisosterism to Raise Potency and Selectivity toward P-Glycoprotein,” Journal of Medicinal Chemistry 57, no. 23 (2014): 9983–94.
  • J. Schulz, F. Horký, I. Císařová, and P. Štěpnićka, “Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands,” Catalysts 7, (2017): 167–86.
  • M. Ballantine, M. L. Menard, and W. Tam, “Isomerization of 7-Oxabenzonorbornadienes into Naphthols Catalyzed by [RuCl2(CO)3]2,” The Journal of Organic Chemistry 74, no. 19 (2009): 7570–3.
  • Y. Zhang, S. Liu, X. Yang, M. Yang, W. Xu, Y. Li, and L. Tao, “Staurosporine Shows Insecticidal Activity against Mythimna Separate Walker (Lepidoptera: Noctuidae) Potentially via Induction of Apoptosis,” Pesticide Biochemistry and Physiology 128, (2016): 37–44.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.