Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

Maryna O. Mazur, Oleksii S. Zhelavskyi, Eugene M. Zviagin, Svitlana V. Shishkina, Vladimir I. Musatov, Maksim A. Kolosov, Elena H. Shvets, Anna Yu. Andryushchenko and Valentyn A. Chebanov
Beilstein J. Org. Chem. 2021, 17, 678–687. https://doi.org/10.3762/bjoc.17.57

Supporting Information

Supporting Information File 1: General synthetic procedures, characteristics of compounds 6 and 7, X-ray experimental data and copies of 1H and 13C NMR spectra.
Format: PDF Size: 6.7 MB Download

Cite the Following Article

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition
Maryna O. Mazur, Oleksii S. Zhelavskyi, Eugene M. Zviagin, Svitlana V. Shishkina, Vladimir I. Musatov, Maksim A. Kolosov, Elena H. Shvets, Anna Yu. Andryushchenko and Valentyn A. Chebanov
Beilstein J. Org. Chem. 2021, 17, 678–687. https://doi.org/10.3762/bjoc.17.57

How to Cite

Mazur, M. O.; Zhelavskyi, O. S.; Zviagin, E. M.; Shishkina, S. V.; Musatov, V. I.; Kolosov, M. A.; Shvets, E. H.; Andryushchenko, A. Y.; Chebanov, V. A. Beilstein J. Org. Chem. 2021, 17, 678–687. doi:10.3762/bjoc.17.57

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: 8.6 MB Download

Citations to This Article

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

Scholarly Works

  • Vaishnani, M. J.; Bijani, S.; Rahamathulla, M.; Baldaniya, L.; Jain, V.; Thajudeen, K. Y.; Ahmed, M. M.; Farhana, S. A.; Pasha, I. Biological importance and synthesis of 1,2,3-triazole derivatives: a review. Green Chemistry Letters and Reviews 2024, 17. doi:10.1080/17518253.2024.2307989
  • Botsula, I.; Sсhavikin, J.; Heinämäki, J.; Laidmäe, I.; Mazur, M.; Raal, A.; Koshovyi, O.; Kireyev, I.; Chebanov, V. Application of nanofiber-based drug delivery systems in improving anxiolytic effect of new 1,2,3-triazolo-1,4-benzodiazepine derivatives. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 2024, 195, 106712. doi:10.1016/j.ejps.2024.106712
  • Luzzio, F. A. Diversity of heterocyclic reactants in the click reaction. Advances in Heterocyclic Chemistry; Elsevier, 2024; pp 95–176. doi:10.1016/bs.aihch.2023.11.002
  • Doraghi, F.; Karimian, S.; Aledavoud, S. P.; Amini, A.; Larijani, B.; Mahdavi, M. 2-azidobenzaldehyde: A versatile scaffold for the generation of N‐heterocyclic compounds. Journal of Molecular Structure 2023, 1294, 136510. doi:10.1016/j.molstruc.2023.136510
  • Yang, M.-L.; Zhao, L.; Chen, H.-R.; Ding, M.-W. Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction. The Journal of organic chemistry 2023, 88, 16424–16434. doi:10.1021/acs.joc.3c01955
  • Chebanov, V. A.; Desenko, S. M.; Lipson, V. V. Heterocycles on the crest of microwaves and ultrasonics in the Institute for Single Crystals of National Academy of Sciences of Ukraine: chemistry and history. Chemistry of Heterocyclic Compounds 2023, 59, 386–405. doi:10.1007/s10593-023-03207-w
  • Damera, T.; Pagadala, R.; Rana, S.; Jonnalagadda, S. B. A Concise Review of Multicomponent Reactions Using Novel Heterogeneous Catalysts under Microwave Irradiation. Catalysts 2023, 13, 1034. doi:10.3390/catal13071034
  • Yang, M.-L.; Zhao, L.; Chen, H.-R.; Ding, M.-W. Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5H-Quinazolino[3,2-a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization. The Journal of organic chemistry 2023, 88, 1898–1906. doi:10.1021/acs.joc.2c02621
  • Bissember, A. C.; Wales, S. M.; Hawkins, B. C.; Chen, J. L.-Y.; Petersen, W. F.; Tague, A. J.; Fleming, C. L.; Cording, A. P.; Bhana, A. D.; Johnstone, M. D.; Shephard, J. P. Seven-membered rings. Progress in Heterocyclic Chemistry; Elsevier, 2023; pp 559–608. doi:10.1016/b978-0-443-18939-5.00016-0
  • P, R.; Thomas, J.; Dehaen, W.; John, J. Advances in the Synthesis of Fused 1,2,3-Triazoles via a MCR-Intramolecular Azide-Alkyne Cycloaddition Approach. Molecules (Basel, Switzerland) 2022, 28, 308. doi:10.3390/molecules28010308
  • Вовк, М. В. Клік-хімія та біоортогональні реакції: прорив в епоху функціональності в хімії. Visnik Nacional noi academii nauk Ukrai ni 2022, 30–43. doi:10.15407/visn2022.12.030
  • Yang, M.-L.; Pan, H.-L.; Kong, H.-H.; Ding, M.-W. One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions. Organic Chemistry Frontiers 2022, 9, 5983–5988. doi:10.1039/d2qo01130a
  • Ding, M.-W.; Yang, M.-L.; Chen, H.-R.; Zhao, L. New Efficient Synthesis of 6,12-Dihydro-5H-quinazolino[3,2-a] quinazolin-5-ones via Ugi/Staudinger/Aza-Wittig/Addition/Nucleophilic Acyl Substitution Sequence. Synthesis 2022, 55, 465–472. doi:10.1055/a-1932-5811
  • Acharjee, N.; Mohammad-Salim, H. A.; Chakraborty, M. Unveiling the synthesis of spirocyclic, tricyclic, and bicyclic triazolooxazines from intramolecular [3 + 2] azide-alkyne cycloadditions with a molecular electron density theory perspective. Structural Chemistry 2022, 33, 555–570. doi:10.1007/s11224-021-01870-3
Other Beilstein-Institut Open Science Activities