Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

Martina Tireli, Silvija Maračić, Stipe Lukin, Marina Juribašić Kulcsár, Dijana Žilić, Mario Cetina, Ivan Halasz, Silvana Raić-Malić and Krunoslav Užarević
Beilstein J. Org. Chem. 2017, 13, 2352–2363. https://doi.org/10.3762/bjoc.13.232

Supporting Information

Supporting Information File 1: Solution synthetic procedures, characterization data, 1H, 13C NMR spectra of 48, NOESY spectrum of 4, high-resolution mass spectra of 58, crystallographic data, FTIR–ATR, and Raman data.
Format: PDF Size: 2.4 MB Download

Cite the Following Article

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole
Martina Tireli, Silvija Maračić, Stipe Lukin, Marina Juribašić Kulcsár, Dijana Žilić, Mario Cetina, Ivan Halasz, Silvana Raić-Malić and Krunoslav Užarević
Beilstein J. Org. Chem. 2017, 13, 2352–2363. https://doi.org/10.3762/bjoc.13.232

How to Cite

Tireli, M.; Maračić, S.; Lukin, S.; Kulcsár, M. J.; Žilić, D.; Cetina, M.; Halasz, I.; Raić-Malić, S.; Užarević, K. Beilstein J. Org. Chem. 2017, 13, 2352–2363. doi:10.3762/bjoc.13.232

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: 182.0 KB Download

Citations to This Article

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

Scholarly Works

  • Flores, A.; Cañamares, D.; Apaza Ticona, L.; Pablos, J. L.; Peña, J.; Hernáiz, M. J. Highly efficient functionalization of hydroxypropyl cellulose with glucuronic acid through click chemistry under microwave irradiation as potential biomaterial with therapeutic properties. Catalysis Today 2024, 429, 114495. doi:10.1016/j.cattod.2023.114495
  • Sumran, G.; Jain, N.; Kumar, P.; Aggarwal, R. Trifluoromethyl-β-dicarbonyls as Versatile Synthons in Synthesis of Heterocycles. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202303599. doi:10.1002/chem.202303599
  • Gomes, C.; Costa, M.; Lopes, S. M. M.; Nogueira, B. A.; Fausto, R.; Paixão, J. A.; Pinho e Melo, T. M. V. D.; Martins, L. M. D. R. S.; Pineiro, M. On the mechanochemical synthesis of C-scorpionates with an oxime moiety and their application in the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction. New Journal of Chemistry 2024, 48, 874–886. doi:10.1039/d3nj05017c
  • Chen, B.; Zhang, M.; Yao, K.; Zhang, C.; Wu, Q.; Hu, T.; Shan, S. Dye-sensitized NH2-UiO-66 anchored with copper ions for tandem visible-light-driven hydrogen evolution. Journal of Environmental Chemical Engineering 2023, 11, 111349. doi:10.1016/j.jece.2023.111349
  • Karmakar, P.; Karmakar, I.; Mukherjee, D.; Bhowmick, A.; Brahmachari, G. Mechanochemical Solvent-Free One-Pot Synthesis of Poly-Functionalized 5-(Arylselanyl)-1H-1,2,3-triazoles Through a Copper(I)-Catalyzed Click Reaction. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202302539. doi:10.1002/chem.202302539
  • Wang, H.; Ding, W.; Zou, G. Mechanoredox/Nickel Co-Catalyzed Cross Electrophile Coupling of Benzotriazinones with Alkyl (Pseudo)halides. The Journal of organic chemistry 2023, 88, 12891–12901. doi:10.1021/acs.joc.3c00681
  • Abd El-Aal, H. A. K. Synthesis of naphtho- and pyrazolo-fused systems by an intramolecular Friedel–Crafts approach. Australian Journal of Chemistry 2023, 76, 760–773. doi:10.1071/ch23030
  • Grover, T.; Singh, N.; Vaja, M. Insights into Quinoline in Context of Conventional versus Green Synthesis. Current Organic Chemistry 2023, 27, 1381–1392. doi:10.2174/0113852728268691231009063856
  • Maračić, S.; Jakopec, S.; Piškor, M.; Leventić, M.; Lapić, J.; Djaković, S.; Cetina, M.; Glavaš‐Obrovac, L.; Raić‐Malić, S. Mechanochemical synthesis and antiproliferative activity of novel ferrocene quinoline/quinolone hybrids. Applied Organometallic Chemistry 2023, 37. doi:10.1002/aoc.7124
  • Chen, M.; Zhang, C.; Tang, Y.; Cai, Q.; Yu, J.; Chen, Y.; He, Y.; Bai, J.; Fu, M.; Chen, S.; Tan, X.; Peng, R.; Liu, X. Cu ions anchored in the porphyrin center act as transient metal centers of 2D-MOFs to enhance photocatalytic hydrogen production. Catalysis Science & Technology 2023, 13, 581–586. doi:10.1039/d2cy01766k
  • Hernáiz, M. J.; Flores, A.; Cañamares, D.; Apaza Ticona, L.; Pablos, J. L.; PEÑA, J. Highly Efficient Functionalization of Cellulose with Glucuronic Acid Through Click Chemistry Under Microwave Irradiation as Potential Biomaterial with Therapeutic Properties. Elsevier BV 2023. doi:10.2139/ssrn.4626577
  • Rajni; Versha; Singh, L.; Rana, R.; Bendi, A. Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review. ChemistrySelect 2022, 7. doi:10.1002/slct.202203648
  • Martinez, V.; Stolar, T.; Karadeniz, B.; Brekalo, I.; Užarević, K. Advancing mechanochemical synthesis by combining milling with different energy sources. Nature reviews. Chemistry 2022, 7, 51–65. doi:10.1038/s41570-022-00442-1
  • Bhattacherjee, D.; Kovalev, I. S.; Kopchuk, D. S.; Rahman, M.; Santra, S.; Zyryanov, G. V.; Das, P.; Purohit, R.; Rusinov, V. L.; Chupakhin, O. N. Mechanochemical Approach towards Multi-Functionalized 1,2,3-Triazoles and Anti-Seizure Drug Rufinamide Analogs Using Copper Beads. Molecules (Basel, Switzerland) 2022, 27, 7784. doi:10.3390/molecules27227784
  • Jones, A. C.; Leitch, J. A.; Raby-Buck, S. E.; Browne, D. L. Mechanochemical techniques for the activation and use of zero-valent metals in synthesis. Nature Synthesis 2022, 1, 763–775. doi:10.1038/s44160-022-00106-4
  • Pickhardt, W.; Beaković, C.; Mayer, M.; Wohlgemuth, M.; Kraus, F. J. L.; Etter, M.; Grätz, S.; Borchardt, L. The Direct Mechanocatalytic Suzuki-Miyaura Reaction of Small Organic Molecules. Angewandte Chemie (International ed. in English) 2022, 61, e202205003. doi:10.1002/anie.202205003
  • Pickhardt, W.; Beaković, C.; Mayer, M.; Wohlgemuth, M.; Kraus, F. J. L.; Etter, M.; Grätz, S.; Borchardt, L. Die direkte mechanokatalytische Suzuki–Miyaura‐Kupplung kleiner organischer Moleküle. Angewandte Chemie 2022, 134. doi:10.1002/ange.202205003
  • Popov, A. B.; Macan, A. M.; Jakopec, S.; Prpić, H.; Hrkać, A. H.; Pavelić, S. K.; Raić-Malić, S. Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation. Future medicinal chemistry 2022, 14, 1187–1202. doi:10.4155/fmc-2022-0047
  • Li, H.; Liu, X.; Song, M.; Feng, H.; Yu, J.; Liu, B.; Ren, Q.; Yang, Z.; Xu, M.; He, Y. Non-noble copper ion anchored on NH2-MIL-101(Fe) as a novel cocatalyst with transient metal centers for efficient photocatalytic water splitting. Journal of Alloys and Compounds 2022, 905, 164153. doi:10.1016/j.jallcom.2022.164153
  • García-Oliva, C.; Merchán, A.; Perona, A.; Hoyos, P.; Rumbero, Á.; Hernáiz, M. J. Development of sustainable synthesis of glucuronic acid glycodendrimers using ball milling and microwave-assisted CuAAC reaction. New Journal of Chemistry 2022, 46, 6389–6393. doi:10.1039/d1nj06132a
Other Beilstein-Institut Open Science Activities