MAIN AND BY-PROCESSES AT 1-(2-NITROARYL)-1H-BENZOTRIAZOLE REDUCTION
Аннотация и ключевые слова
Аннотация (русский):
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.

Ключевые слова:
reduction, condensation, alkylation, 1-(2-aminoaryl)-1H-benzotriazoles, azoxybenzene, alkylamines
Текст
Текст произведения (PDF): Читать Скачать
Список литературы

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/.

Войти или Создать
* Забыли пароль?