Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

Rodrigo Abonia, Luisa F. Gutiérrez, Braulio Insuasty, Jairo Quiroga, Kenneth K. Laali, Chunqing Zhao, Gabriela L. Borosky, Samantha M. Horwitz and Scott D. Bunge
Beilstein J. Org. Chem. 2019, 15, 642–654. https://doi.org/10.3762/bjoc.15.60

Supporting Information

Supporting Information File 1: Spectroscopic data for compounds 8 and 9, copies of NMR spectra and additional Table and Figures.
Format: PDF Size: 26.3 MB Download
Supporting Information File 2: CIF report for 9{4,7,1}.
Format: PDF Size: 197.7 KB Download

Cite the Following Article

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
Rodrigo Abonia, Luisa F. Gutiérrez, Braulio Insuasty, Jairo Quiroga, Kenneth K. Laali, Chunqing Zhao, Gabriela L. Borosky, Samantha M. Horwitz and Scott D. Bunge
Beilstein J. Org. Chem. 2019, 15, 642–654. https://doi.org/10.3762/bjoc.15.60

How to Cite

Abonia, R.; Gutiérrez, L. F.; Insuasty, B.; Quiroga, J.; Laali, K. K.; Zhao, C.; Borosky, G. L.; Horwitz, S. M.; Bunge, S. D. Beilstein J. Org. Chem. 2019, 15, 642–654. doi:10.3762/bjoc.15.60

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: 406.2 KB Download

Citations to This Article

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

Scholarly Works

  • Cologni, R.; Holschbach, M.; Schneider, D.; Bier, D.; Schulze, A.; Stegmayr, C.; Endepols, H.; Ermert, J.; Neumaier, F.; Neumaier, B. Preparation and Preclinical Evaluation of 18F-Labeled Olutasidenib Derivatives for Non-Invasive Detection of Mutated Isocitrate Dehydrogenase 1 (mIDH1). Molecules (Basel, Switzerland) 2024, 29, 3939. doi:10.3390/molecules29163939
  • Chaithra, N.; Swarup, H. A.; Chandrasekhar, S.; Jayanna, B.; Kumara, K.; Mantelingu, K.; Lokanath, N. Regioselective benzylation of imidazo[1,5-a]pyridines and indoles via iodine catalyzed reaction using alcohols - An approach to crystal structure prediction, DFT studies and Hirshfeld surface analysis. Journal of Molecular Structure 2024, 1295, 136591. doi:10.1016/j.molstruc.2023.136591
  • Pasricha, S.; Mittal, K.; Gahlot, P.; Kaur, H.; Avasthi, N.; Shweta. Multicomponent synthetic strategies and perspectives for synthesis of linked or fused coumarin heterocycles. Journal of the Iranian Chemical Society 2022, 19, 4035–4092. doi:10.1007/s13738-022-02603-x
  • Verma, M.; Thakur, A.; Sharma, R.; Bharti, R. Recent Advancement in the One-pot Synthesis of the Tri-substituted Methanes (TRSMs) and their Biological Applications. Current organic synthesis 2022, 19, 86–114. doi:10.2174/1570179418666210910105342
  • Mizuta, S.; Otaki, H.; Ishikawa, T.; Makau, J. N.; Yamaguchi, T.; Fujimoto, T.; Takakura, N.; Sakauchi, N.; Kitamura, S.; Nono, H.; Nishi, R.; Tanaka, Y.; Takeda, K.; Nishida, N.; Watanabe, K. Lead Optimization of Influenza Virus RNA Polymerase Inhibitors Targeting PA-PB1 Interaction. Journal of medicinal chemistry 2021, 65, 369–385. doi:10.1021/acs.jmedchem.1c01527
  • Ghashghaei, O.; Pedrola, M.; Escolano, C.; Lavilla, R. Multicomponent Reactions towards Heterocycles; Wiley, 2021; pp 1–43. doi:10.1002/9783527832439.ch1
  • Khanna, L.; Mansi; Yadav, S.; Misra, N.; Khanna, P. “In water” synthesis of bis(indolyl)methanes: a review. Synthetic Communications 2021, 51, 2892–2923. doi:10.1080/00397911.2021.1957113
  • Shatokhin, S. S.; Tuskaev, V. A.; Gagieva, S. C.; Oganesyan, E. T. Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone. Russian chemical bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 2021, 70, 1011–1045. doi:10.1007/s11172-021-3183-6
  • Baruah, B.; Deb, M. L. Catalyst-free and additive-free reactions enabling C–C bond formation: a journey towards a sustainable future. Organic & biomolecular chemistry 2021, 19, 1191–1229. doi:10.1039/d0ob02149k
  • Cheruku, S.; Nagaraju, C.; Shetty, P.; A, S. H.; C, S. N.; N, K. M.; Kempegowda, M. An efficient synthesis of medicinally important indole based triarylmethanes by using propylphosphonic anhydride (T3P. Synthetic Communications 2020, 50, 1486–1494. doi:10.1080/00397911.2020.1743319

Patents

  • EYMERY MATHIAS; MCCARTHY ANDREW; BOUMENDJEL AHCÈNE. NOVEL CANNABINOID-INSPIRED INHIBITORS OF AUTOTAXIN. WO 2024133360 A1, June 27, 2024.
Other Beilstein-Institut Open Science Activities