Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach

Florian Boeck, Max Blazejak, Markus R. Anneser and Lukas Hintermann
Beilstein J. Org. Chem. 2012, 8, 1630–1636. https://doi.org/10.3762/bjoc.8.186

Supporting Information

Supporting Information File 1: Experimental procedures, characterization data and copies of NMR spectra.
Format: PDF Size: 1002.2 KB Download

Cite the Following Article

Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
Florian Boeck, Max Blazejak, Markus R. Anneser and Lukas Hintermann
Beilstein J. Org. Chem. 2012, 8, 1630–1636. https://doi.org/10.3762/bjoc.8.186

How to Cite

Boeck, F.; Blazejak, M.; Anneser, M. R.; Hintermann, L. Beilstein J. Org. Chem. 2012, 8, 1630–1636. doi:10.3762/bjoc.8.186

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

  • Amer, S.; Joseph, V.; Oded, B.-E.; Marks, V.; Grynszpan, F.; Levine, M. Shining light on fluoride detection: a comprehensive study exploring the potential of coumarin precursors as selective turn-on fluorescent chemosensors. Organic & biomolecular chemistry 2023, 21, 9410–9415. doi:10.1039/d3ob01563g
  • Neveselý, T.; Wienhold, M.; Molloy, J. J.; Gilmour, R. Advances in the E → Z Isomerization of Alkenes Using Small Molecule Photocatalysts. Chemical reviews 2021, 122, 2650–2694. doi:10.1021/acs.chemrev.1c00324
  • Juang, S.-H.; Hsieh, M.-T.; Hsu, P. L.; Chen, J. L.; Liu, H. K.; Liang, F. P.; Kuo, S.-C.; Chiu, C. Y.; Liu, S.-H.; Chou, C. H.; Wu, T. S.; Hung, H. Y. Studies of Coumarin Derivatives for Constitutive Androstane Receptor (CAR) Activation. Molecules (Basel, Switzerland) 2020, 26, 164. doi:10.3390/molecules26010164
  • Huang, Y.; Liao, J.; Wang, W.; Liu, H.; Guo, H. Synthesis of heterocyclic compounds through nucleophilic phosphine catalysis. Chemical communications (Cambridge, England) 2020, 56, 15235–15281. doi:10.1039/d0cc05699e
  • Huong, T. V.; Giang, P. M.; Trang, V. M. Coumarins and Polar Constituents from Eupatorium triplinerve and Evaluation of Their α-Glucosidase Inhibitory Activity. Journal of Chemistry 2020, 2020, 1–8. doi:10.1155/2020/8945063
  • Cervi, A.; Vo, Y. T.-H.; Chai, C. L. L.; Banwell, M. G.; Lan, P.; Willis, A. C. Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2H-Chromenes. The Journal of organic chemistry 2020, 86, 178–198. doi:10.1021/acs.joc.0c02011
  • Wienhold, M.; Molloy, J. J.; Daniliuc, C. G.; Gilmour, R. Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3 -Synthons. Angewandte Chemie (International ed. in English) 2020, 60, 685–689. doi:10.1002/anie.202012099
  • Wienhold, M.; Molloy, J. J.; Daniliuc, C. G.; Gilmour, R. Coumarins by Direct Annulation: β‐Borylacrylates as Ambiphilic C3‐Synthons. Angewandte Chemie 2020, 133, 695–699. doi:10.1002/ange.202012099
  • Vanammoole, L.; Kommera, R.; Kurma, S. H.; Vaidya, J. R.; Bhimapaka, C. R. Regioselective Halogenation of 2H-Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H-Chromenone Natural Products. ChemistrySelect 2020, 5, 8875–8880. doi:10.1002/slct.202000908
  • Neveselý, T.; Daniliuc, C. G.; Gilmour, R. Sequential Energy Transfer Catalysis: A Cascade Synthesis of Angularly-Fused Dihydrocoumarins. Organic letters 2019, 21, 9724–9728. doi:10.1021/acs.orglett.9b03882
  • Vasconcelos, S. N. S.; de Oliveira, I. M.; Shamim, A.; Zukerman-Schpector, J.; Pimenta, D. C.; Stefani, H. A. Stereoselective Oxa‐Michael Addition of Tyrosine to Propargyl Aldehyde/Esters: Formation of Benzofurans and Flavones. Advanced Synthesis & Catalysis 2019, 361, 4243–4254. doi:10.1002/adsc.201900564
  • Yoon, J.; Cheon, C. H. Synthesis of 2‐Arylquinolines from 2‐Iodoanilines and β‐Chloropropiophenones via Palladium‐Catalyzed Cascade Reaction. Asian Journal of Organic Chemistry 2019, 8, 1631–1636. doi:10.1002/ajoc.201900290
  • Jeon, J.; Lee, S. Y.; Cheon, C. H. tert-Butoxide-Mediated Synthesis of 3,4′-Biquinolines from 2-Aminochalcones. Advanced Synthesis & Catalysis 2019, 361, 2360–2364. doi:10.1002/adsc.201900029
  • Harish, B.; Subbireddy, M.; Obulesu, O.; Suresh, S. One-Pot Allylation-Intramolecular Vinylogous Michael Addition-Isomerization Cascade of o-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives. Organic letters 2019, 21, 1823–1827. doi:10.1021/acs.orglett.9b00414
  • Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Phosphine Organocatalysis. Chemical reviews 2018, 118, 10049–10293. doi:10.1021/acs.chemrev.8b00081
  • Schmidt, B.; Schultze, C. A One‐Pot Synthesis of Pyranocoumarins Through Microwave‐Promoted Propargyl Claisen Rearrangement/Wittig Olefination. European Journal of Organic Chemistry 2018, 2018, 223–227. doi:10.1002/ejoc.201701684
  • Zhan, K.; Li, Y. Visible-Light Photocatalytic E to Z Isomerization of Activated Olefins and Its Application for the Syntheses of Coumarins. Catalysts 2017, 7, 337. doi:10.3390/catal7110337
  • Konrádová, D.; Kozubíková, H.; Doležal, K.; Pospisil, J. Microwave‐Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol. European Journal of Organic Chemistry 2017, 2017, 5204–5213. doi:10.1002/ejoc.201701021
  • Acharya, A.; Gautam, V.; Ila, H. Synthesis of Thieno-Fused Five- and Six-Membered Nitrogen and Oxygen Heterocycles via Intramolecular Heteroannulation of 4,5-Substituted 3-Amino or 3-Hydroxy 2-Functionalized Thiophenes. The Journal of organic chemistry 2017, 82, 7920–7938. doi:10.1021/acs.joc.7b01153
  • Sachdev, D. Silica polymer nanocomposites functionalized with polyphosphoric acid: A mild catalyst for efficient one-pot synthesis of dihydropyrimidinones under environmentally benign conditions. Inorganic and Nano-Metal Chemistry 2017, 47, 1110–1116. doi:10.1080/24701556.2016.1241268
Other Beilstein-Institut Open Science Activities