[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions

Stephan Cludius-Brandt, Lukas Kupracz and Andreas Kirschning
Beilstein J. Org. Chem. 2013, 9, 1745–1750. https://doi.org/10.3762/bjoc.9.201

Supporting Information

Supporting Information File 1: Descriptions on the synthesis and analyses of vinyl azides and as well as on cycloaddition products.
Format: PDF Size: 1.2 MB Download

Cite the Following Article

[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
Stephan Cludius-Brandt, Lukas Kupracz and Andreas Kirschning
Beilstein J. Org. Chem. 2013, 9, 1745–1750. https://doi.org/10.3762/bjoc.9.201

How to Cite

Cludius-Brandt, S.; Kupracz, L.; Kirschning, A. Beilstein J. Org. Chem. 2013, 9, 1745–1750. doi:10.3762/bjoc.9.201

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

  • Lin, S.; Chu, Y.; Deng, J.; Xie, F.; Zhao, L. Light-induced synthesis of 2H-azirines and its applications in organic chemistry. Journal of Saudi Chemical Society 2024, 28, 101831. doi:10.1016/j.jscs.2024.101831
  • Nunes, C. M.; Lopes Jesus, A. J.; Rosado, M. T. S.; Fausto, R. On the Carbenic Nature of Nitrile Ylides: Experimental and Computational Characterization of Hydroxy and Amino Nitrile Ylides. European Journal of Organic Chemistry 2023, 27. doi:10.1002/ejoc.202301103
  • Saxena, B.; Patel, R. I.; Tripathi, J.; Sharma, A. Visible light-assisted chemistry of vinyl azides and its applications in organic synthesis. Organic & biomolecular chemistry 2023, 21, 4723–4743. doi:10.1039/d3ob00588g
  • Schulz, G.; George, V.; Taser, D.; Kirschning, A. Taming Bromine Azide for Use in Organic Solvents─Radical Bromoazidations and Alcohol Oxidations. The Journal of organic chemistry 2023, 88, 3781–3786. doi:10.1021/acs.joc.2c03012
  • Saleh, L. Y.; Altıntaş, B.; Filiciotto, L.; Zorlu, Y.; Luque, R.; Ülger, M.; Döndaş, H. A.; Altug, C. Structural assessment of novel spiro-naphthalene-1.2'- [1,3,4]oxadiazol-4-ones prepared under batch and flow chemistry with a concise antifungal and anti(myco)bacterial activity. Tetrahedron 2023, 131, 133231. doi:10.1016/j.tet.2022.133231
  • Sakharov, P. A.; Rostovskii, N. V.; Khlebnikov, A. F.; Novikov, M. S. Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds. Molecules (Basel, Switzerland) 2022, 27, 5681. doi:10.3390/molecules27175681
  • De, A.; Majee, A. Synthesis of Various Functionalized 2 H ‐azirines‐An Updated Library. Journal of Heterocyclic Chemistry 2021, 59, 422–448. doi:10.1002/jhet.4415
  • Wang, Z.; Li, H.; Wang, Z.; Suleman, M.; Wang, Y.; Lu, P. Photocatalytic Approach for Construction of 5,6-Dihydroimidazo[2,1-a]isoquinolines and Their Luminescent Properties. The Journal of organic chemistry 2021, 86, 8101–8111. doi:10.1021/acs.joc.1c00590
  • Gambacorta, G.; Sharley, J. S.; Baxendale, I. R. A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries. Beilstein journal of organic chemistry 2021, 17, 1181–1312. doi:10.3762/bjoc.17.90
  • Alfano, A. I.; Brindisi, M.; Lange, H. Flow synthesis approaches to privileged scaffolds – recent routes reviewed for green and sustainable aspects. Green Chemistry 2021, 23, 2233–2292. doi:10.1039/d0gc03883k
  • Kösel, T.; Dräger, G.; Kirschning, A. Oxidative azidations of phenols and ketones using iodine azide after release from an ion exchange resin. Organic & biomolecular chemistry 2021, 19, 2907–2911. doi:10.1039/d1ob00083g
  • Livingstone, K.; Little, G.; Jamieson, C. Recent Advances in the Generation of Nitrilium Betaine 1,3-Dipoles. Synthesis 2021, 53, 2395–2407. doi:10.1055/a-1389-1281
  • Andresini, M.; Degannaro, L.; Luisi, R. A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach. Beilstein journal of organic chemistry 2021, 17, 203–209. doi:10.3762/bjoc.17.20
  • Vuillermet, F.; Bourret, J.; Pelletier, G. Synthesis of Imidazo[1,2-a]pyridines: Triflic Anhydride-Mediated Annulation of 2H-Azirines with 2-Chloropyridines. The Journal of organic chemistry 2020, 86, 388–402. doi:10.1021/acs.joc.0c02148
  • Plumet, J. 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides under “Non-Conventional” Conditions: Green Solvents, Irradiation, and Continuous Flow. ChemPlusChem 2020, 85, 2252–2271. doi:10.1002/cplu.202000448
  • García-Lacuna, J.; Domínguez, G.; Pérez-Castells, J. Flow Chemistry for Cycloaddition Reactions. ChemSusChem 2020, 13, 5138–5163. doi:10.1002/cssc.202001372
  • Kösel, T.; Schulz, G.; Dräger, G.; Kirschning, A. Photochemische Transformationen mit Iodazid nach Freisetzung von einem Ionenaustauscherharz. Angewandte Chemie 2020, 132, 12475–12479. doi:10.1002/ange.202003079
  • Kösel, T.; Schulz, G.; Dräger, G.; Kirschning, A. Photochemical Transformations with Iodine Azide after Release from an Ion Exchange Resin. Angewandte Chemie (International ed. in English) 2020, 59, 12376–12380. doi:10.1002/anie.202003079
  • Krell, K.; Harijan, D.; Ganz, D.; Doll, L.; Wagenknecht, H.-A. Postsynthetic Modifications of DNA and RNA by Means of Copper-Free Cycloadditions as Bioorthogonal Reactions. Bioconjugate chemistry 2020, 31, 990–1011. doi:10.1021/acs.bioconjchem.0c00072
  • Angyal, A.; Demjén, A.; Wölfling, J.; Puskás, L. G.; Kanizsai, I. Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2H-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles. The Journal of organic chemistry 2020, 85, 3587–3595. doi:10.1021/acs.joc.9b03288
Other Beilstein-Institut Open Science Activities