Abstract:
An original synthesis of a new non-symmetric energetic ABB' type monomer, 2-azido-4-propargylamino-6- propargyloxy-s-triazine, with a total yield of 40% involves the sequential introduction of propargylamino, propargyloxy and azido groups into s-triazine. DFT investigation of azide- Cl alkyne cycloaddition mechanism at M06-2X/6-311++G(d,p) level of theory for this monomer predicts that the regioselectivity of polycycloaddition reaction should increase with the number of propargylamino groups in the monomer structure due to the stabilization of the transition state, leading to 1,5-triazole regioisomer.
Citation:
A. O. Petrov, S. V. Karpov, G. V. Malkov, A. V. Shastin, E. R. Badamshina, “New non-symmetric azido-diacetylenic s-triazine monomer for polycycloaddition”, Mendeleev Commun., 32:4 (2022), 464–466
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https://www.mathnet.ru/eng/mendc696
https://www.mathnet.ru/eng/mendc/v32/i4/p464
This publication is cited in the following 7 articles:
Pavel S. Gribov, Natalia N. Il'icheva, Natalia N. Kondakova, Evgenia R. Stepanova, Anatoly P. Denisyuk, Vladimir A. Sizov, Varvara D. Dotsenko, Valery P. Sinditskii, Aleksei B. Sheremetev, “Nitramino-polymer with ether bridges and 1,2,3-triazole subunits incorporated into the polymer chain”, FirePhysChem, 5:1 (2025), 15
Sergei V. Karpov, Artem Iakunkov, Dmitry A. Chernyaev, Vladimir G. Kurbatov, Georgiy V. Malkov, Elmira R. Badamshina, “A Theoretical Investigation of the Polyaddition of an AB2+A2+B4 Monomer Mixture”, Polymers, 16:3 (2024), 426
A. O. Petrov, S. V. Karpov, A. V. Darovskikh, A. S. Dzhalmukhanova, T. A. Pugacheva, V. A. Garanin, D. B. Lempert, L. S. Yanovskii, G. V. Malkov, E. R. Badamshina, “Calculation of thermochemical and detonation parameters of azidoacetylene derivatives of s-triazine”, Combustion, Explosion and Shock Waves, 59:6 (2023), 707–715
Pierre Audebert, Vincent Sol, Progress in Heterocyclic Chemistry, 35, 2023, 471
Anna V. Tsyganova, Artem O. Petrov, Alexey V. Shastin, Natalia V. Filatova, Victoria A. Mumyatova, Alexander E. Tarasov, Alina V. Lolaeva, Georgiy V. Malkov, “Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers”, Chemistry, 6:1 (2023), 1
Pavel S. Gribov, Natalia N. Kondakova, Natalia N. Il'icheva, Evgenia R. Stepanova, Anatoly P. Denisyuk, Vladimir A. Sizov, Varvara D. Dotsenko, Dmitry B. Vinogradov, Pavel V. Bulatov, Valery P. Sinditskii, Kyrill Yu. Suponitsky, Mikhail M. Il'in, Mukhamed L. Keshtov, Aleksei B. Sheremetev, “Energetic Polymer Possessing Furazan, 1,2,3-Triazole, and Nitramine Subunits”, IJMS, 24:11 (2023), 9645
P. S. Gribov, T. S. Kon'kova, K. Yu. Suponitsky, A. B. Sheremetev, “Dipropargyl ethers possessing nitramine units”, Mendeleev Commun., 33:4 (2023), 466–468
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