Ярославский государственный университет им. П.Г. Демидова (Доцент)
Ярославль, Ярославская область, Россия
с 01.01.2025 по настоящее время
Ярославский государственный университет им. П.Г. Демидова (Студент)
Ярославль, Ярославская область, Россия
Ярославль, Ярославская область, Россия
The paper investigates the HCl concentration impact on the main and by-processes during the reduction of 1-(2-nitroaryl)-1H-benzotriazole by tin (II) chloride in acidic aqueous-alcoholic medium. The authors have observed the formation of azoxy compounds in addition to the target amino derivative at low HCl content in the reaction mass. The use of 36% hydrochloric acid causes the alkylation of the formed amino compound with alcohol as a solvent.
reduction, condensation, alkylation, 1-(2-aminoaryl)-1H-benzotriazoles, azoxybenzene, alkylamines
1. Begunov, R.S., Shebunina, T.V., Yakovleva, Y.S. & Firgang, S.I. (2013) An interesting recyclization in the course of reduction of 1-(2-nitro-4-R-phenyl)-1H-benzimidazoles with tin(II) chloride, Mendeleev Commun, 23(6), pp. 354-355. DOI:https://doi.org/10.1016/j.mencom.2013.11.018.
2. Begunov, R.S., Sokolov, A.A. & Fakhrutdinov, A.N. (2020) Recyclization-isomerization in the reduction of 1-(2-nitro(het)aryl)benzimidazoles, ChemistrySelect, 5(12), pp. 3544-3550. DOI:https://doi.org/10.1002/slct.201904898.
3. Begunov, R.S., Chetvertakova, A.V. & Neganova, M.E. (2023) Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines, Mendeleev Communications, 33(5), pp. 650-652. DOI:https://doi.org/10.1016/j.mencom.2023.09.020.
4. Corona, P., Piras, S., Ibba, R., Riu, F., Murineddu, G., Sanna, G., Madeddu, S., Delogu, I., Loddo, R. & Carta, A. (2020) Antiviral Activity of Benzotriazole Based Derivatives, The Open Medicinal Chemistry Journal, 14(1), pp. 83-98. DOI:https://doi.org/10.2174/1874104502014010083.
5. Piras, S., Sanna, G., Carta, A., Corona, P., Ibba, R., Loddo, R., Madeddu, S., Caria, P., Aulic, S., Laurini, E., Fermeglia, M. & Pricl, S. (2019) Dichloro-Phenyl-Benzotriazoles: A New Selective Class of Human Respiratory Syncytial Virus Entry Inhibitors, Frontiers in Chemistry, 7, pp. 247. DOI:https://doi.org/10.3389/fchem.2019.00247.
6. Ibba, R., Piras, S., Corona, P., Riu, F., Loddo, R., Delogu, I., Collu, G., Sanna, G., Caria, P., Dettori, T. & Carta, A. (2021) Synthesis, Antitumor and Antiviral In Vitro Activities of New Benzotriazole-Dicarboxamide Derivatives, Frontiers in Chemistry, 9, Art. 660424. DOI:https://doi.org/10.3389/fchem.2021.660424.
7. Wu, C.Y., King, K.Y., Kuo, C.J., Fang, J.M., Wu, Y.T., Ho, M.Y., Liao, C.L., Shie, J.J., Liang, P.H. & Wong, C.H. (2006) Stable benzotriazole esters as mechanism-based inactivators of the severe acute respiratory syndrome 3CL protease, Chemistry & Biology, 13(3), pp. 261-268. DOI:https://doi.org/10.1016/j.chembiol.2005.12.008.
8. Santa María, M.D., Claramunt, R.M., Garcia, M.A. & Elguero, J. (2007) Synthesis, structure, and isomerism of N-2,4-dinitrophenylbenzotriazoles, Tetrahedron, 63(18), pp. 3737-3744. DOI:https://doi.org/10.1016/j.tet.2007.02.083.
9. Wilshire, J.F.K. (1966) The reaction of 1-fluoro-2,4-dinitrobenzene with some NH-heteroaromatic compounds, Aust. J. Chem., 19(10), pp. 935-1945. DOI:https://doi.org/10.1071/CH9661935.
10. Bogdanova, D.M., Savina, L.I. & Begunov, R.S. (2022) Synthesis and functionalization of pyrido[1,2-a]benzimidazole amino derivatives, From Chemistry Towards Technology Step-By-Step, 3(4), pp. 30-38 [online]. Available at: http://chemintech.ru/index.php/tor/2022-3-4 (accessed 10.12.2023) (in Russian).
11. Bogdanova, D.M., Savina, L.I. & Begunov, R.S. (2023) Orientation of benzophenone dinitro derivatives mono-reduction, From Chemistry Towards Technology Step-By-Step, 4(1), pp. 43-50 [online]. Available at: http://che-mintech.ru/index.php/tor/2023 (accessed 10.12.2023) (in Russian).
12. Chen, Y.F., Chen, J., Lin, L.J. & Chuang, G.J. (2017) Synthesis of azoxybenzenes by reductive dimerization of nitrosobenzene, J. Org. Chem., 82(21), pp. 11626-11630. DOI:https://doi.org/10.1021/acs.joc.7b01887.
13. Yang, F., Wang, Z., Zhang, X., Jiang, L., Li, Y. & Wang, L. (2015) A green chemoenzymatic process for the synthesis of azoxybenzenes, ChemCatChem., 7(21), pp. 3450-3453. DOI:https://doi.org/10.1002/cctc.201500720/.



