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Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines

Roman Sergeevich Begunov 1
Roman Sergeevich Begunov
, 
Anna Vasil'evna Chetvertakova 1
Anna Vasil'evna Chetvertakova
, 
Margarita Evgenievna Neganova 2, 3
Margarita Evgenievna Neganova
1 P.G. Demidov Yaroslavl State University, Yaroslavl, Russian Federation
2 Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
3 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
10.1016/j.mencom.2023.09.020
Published 2023-09-01
Communication , Volume 33, Issue 5, 650-652
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Begunov R. S., Chetvertakova A. V., Neganova M. E. Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 650-652.
GOST all authors (up to 50) Copy
Begunov R. S., Chetvertakova A. V., Neganova M. E. Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 650-652.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.020
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.020
TI - Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines
T2 - Mendeleev Communications
AU - Begunov, Roman Sergeevich
AU - Chetvertakova, Anna Vasil'evna
AU - Neganova, Margarita Evgenievna
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 650-652
IS - 5
VL - 33
ER -
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@article{2023_Begunov,
author = {Roman Sergeevich Begunov and Anna Vasil'evna Chetvertakova and Margarita Evgenievna Neganova},
title = {Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.020},
number = {5},
pages = {650--652},
doi = {10.1016/j.mencom.2023.09.020}
}
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Begunov, Roman Sergeevich, et al. “Regioselective synthesis of 2-(1H-benzimidazol-1-yl)-5-nitro- and 2-(5-nitro-1H-benzimidazol-1-yl)anilines.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 650-652. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.020.

Keywords

benzimidazole derivatives
nitroanilines
recyclization–isomerization
regioselective reduction
titanium trichloride.

Abstract

The efficiency of two strategies for the synthesis of N-(2-aminophenyl)-5-nitrobenzimidazole derivatives was studied. The promising route involves the stages of 1-(2,4-dinitro-phenyl)-1H-benzimidazole monoreduction at 2-positioned nitro group and tandem conversion involving recyclization of the intermediate N-(2-amino-4-nitrophenyl)-5-nitrobenz-imidazole.

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