Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

Magnus Mortén, Martin Hennum and Tore Bonge-Hansen
Beilstein J. Org. Chem. 2015, 11, 1944–1949. https://doi.org/10.3762/bjoc.11.210

Supporting Information

Supporting Information File 1: Experimental procedures and characterization of compounds.
Format: PDF Size: 936.5 KB Download

Cite the Following Article

Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
Magnus Mortén, Martin Hennum and Tore Bonge-Hansen
Beilstein J. Org. Chem. 2015, 11, 1944–1949. https://doi.org/10.3762/bjoc.11.210

How to Cite

Mortén, M.; Hennum, M.; Bonge-Hansen, T. Beilstein J. Org. Chem. 2015, 11, 1944–1949. doi:10.3762/bjoc.11.210

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.

Citations to This Article

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

Scholarly Works

  • Fujimoto, H.; Tobisu, M. Single‐Carbon Atom Doping Reactions Using Atomic Carbon and Its Equivalents. ChemistryEurope 2024. doi:10.1002/ceur.202400005
  • Schmitt, H. L.; Martymianov, D.; Green, O.; Delcaillau, T.; Park Kim, Y. S.; Morandi, B. Regiodivergent Ring-Expansion of Oxindoles to Quinolinones. Journal of the American Chemical Society 2024, 146, 4301–4308. doi:10.1021/jacs.3c12119
  • Li, C.; Chen, L.; Wang, H.; Yan, Z.; Lyu, B.; Lyu, W.; Jiang, C.; Lu, D.; Li, J.; Jiao, N.; Song, S. C—F Bond Insertion into Indoles with CHBr2F: An Efficient Method to Synthesize Fluorinated Quinolines and Quinolones. Chinese Journal of Chemistry 2024. doi:10.1002/cjoc.202400033
  • Zhang, X.; Su, W.; Guo, H.; Fang, P.; Yang, K.; Song, Q. N‐Heterocycle‐Editing to Access Fused‐BN‐Heterocycles via Ring‐Opening/C−H Borylation/Reductive C−B Bond Formation. Angewandte Chemie 2024, 136. doi:10.1002/ange.202318613
  • Zhang, X.; Su, W.; Guo, H.; Fang, P.; Yang, K.; Song, Q. N-Heterocycle-Editing to Access Fused-BN-Heterocycles via Ring-Opening/C-H Borylation/Reductive C-B Bond Formation. Angewandte Chemie (International ed. in English) 2024, 63, e202318613. doi:10.1002/anie.202318613
  • Wu, F.-P.; Chintawar, C. C.; Lalisse, R.; Mukherjee, P.; Dutta, S.; Tyler, J.; Daniliuc, C. G.; Gutierrez, O.; Glorius, F. Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion. Nature Catalysis 2024, 7, 242–251. doi:10.1038/s41929-023-01089-x
  • Guo, H.; Qiu, S.; Xu, P. One‐Carbon Ring Expansion of Indoles and Pyrroles: A Straightforward Access to 3‐Fluorinated Quinolines and Pyridines. Angewandte Chemie 2023, 136. doi:10.1002/ange.202317104
  • Guo, H.; Qiu, S.; Xu, P. One-Carbon Ring Expansion of Indoles and Pyrroles: A Straightforward Access to 3-Fluorinated Quinolines and Pyridines. Angewandte Chemie (International ed. in English) 2023, 63, e202317104. doi:10.1002/anie.202317104
  • Zhang, B.; Erb, F. R.; Vasilopoulos, A.; Voight, E. A.; Alexanian, E. J. General Synthesis of N-Alkylindoles from N,N-Dialkylanilines via [4 + 1] Annulative Double C-H Functionalization. Journal of the American Chemical Society 2023, 145, 26540–26544. doi:10.1021/jacs.3c10751
  • Zhang, C.; Wan, J.-P. Synthesis of Hypervalent Iodine Diazo Compounds and Their Application in Organic Synthesis. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 30, e202302718. doi:10.1002/chem.202302718
  • Cornella, J.; Spinnato, D.; Leutzsch, M.; Wang, F. Internal Atom Exchange in Oxazole Rings: A Blueprint for Azole Scaffold Evaluation. Synlett 2023. doi:10.1055/a-2201-9285
  • Li, L.; Mi, C.; Huang, G.; Huang, M.; Zhu, Y.; Ni, S.-F.; Wang, Z.; Huang, Y. A Carbene Relay Strategy for Cascade Insertion Reactions. Angewandte Chemie (International ed. in English) 2023, 62, e202312793. doi:10.1002/anie.202312793
  • Li, L.; Mi, C.; Huang, G.; Huang, M.; Zhu, Y.; Ni, S.; Wang, Z.; Huang, Y. A Carbene Relay Strategy for Cascade Insertion Reactions. Angewandte Chemie 2023, 135. doi:10.1002/ange.202312793
  • Wang, H.; Shao, H.; Das, A.; Dutta, S.; Chan, H. T.; Daniliuc, C.; Houk, K. N.; Glorius, F. Dearomative ring expansion of thiophenes by bicyclobutane insertion. Science (New York, N.Y.) 2023, 381, 75–81. doi:10.1126/science.adh9737
  • Joynson, B. W.; Cumming, G. R.; Ball, L. T. Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment. Angewandte Chemie 2023, 135. doi:10.1002/ange.202305081
  • Joynson, B. W.; Cumming, G. R.; Ball, L. T. Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment. Angewandte Chemie (International ed. in English) 2023, 62, e202305081. doi:10.1002/anie.202305081
  • Strunk, K.; Reiser, O. Heterocycles from Cyclopropanation of Five-Membered Heteroarenes. Topics in Heterocyclic Chemistry; Springer International Publishing, 2023; pp 157–185. doi:10.1007/7081_2023_65
  • Palomo, E.; Sharma, A. K.; Wang, Z.; Jiang, L.; Maseras, F.; Suero, M. G. Generating Fischer-Type Rh-Carbenes with Rh-Carbynoids. Journal of the American Chemical Society 2023, 145, 4975–4981. doi:10.1021/jacs.3c00012
  • Joynson, B. W.; Ball, L. T. Skeletal Editing: Interconversion of Arenes and Heteroarenes. Helvetica Chimica Acta 2023, 106. doi:10.1002/hlca.202200182
  • Fujimoto, H. Recent Progress in Ring-Expansion by Single Atom Editing. Journal of Synthetic Organic Chemistry, Japan 2023, 81, 139–140. doi:10.5059/yukigoseikyokaishi.81.139
Other Beilstein-Institut Open Science Activities