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Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes

Roman Sergeevich Begunov 1
Roman Sergeevich Begunov
, 
Valeriya Olegovna Sakulina 1
Valeriya Olegovna Sakulina
, 
Mikhail Aleksandrovich Syroeshkin 2
Mikhail Aleksandrovich Syroeshkin
, 
Evgeniya A Saverina 2
Evgeniya A Saverina
, 
Alexandr Andreevich Sokolov 1
Alexandr Andreevich Sokolov
, 
10.1016/j.mencom.2020.09.027
Published 2020-08-31
Communication , Volume 30, Issue 5, 633-635
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Begunov R. S. et al. Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 633-635.
GOST all authors (up to 50) Copy
Begunov R. S., Sakulina V. O., Syroeshkin M. A., Saverina E. A., Sokolov A. A., Minyaev M. E. Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 633-635.
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TY - JOUR
DO - 10.1016/j.mencom.2020.09.027
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.027
TI - Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes
T2 - Mendeleev Communications
AU - Begunov, Roman Sergeevich
AU - Sakulina, Valeriya Olegovna
AU - Syroeshkin, Mikhail Aleksandrovich
AU - Saverina, Evgeniya A
AU - Sokolov, Alexandr Andreevich
AU - Minyaev, Mikhail Evgenievich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 633-635
IS - 5
VL - 30
ER -
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@article{2020_Begunov,
author = {Roman Sergeevich Begunov and Valeriya Olegovna Sakulina and Mikhail Aleksandrovich Syroeshkin and Evgeniya A Saverina and Alexandr Andreevich Sokolov and Mikhail Evgenievich Minyaev},
title = {Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.027},
number = {5},
pages = {633--635},
doi = {10.1016/j.mencom.2020.09.027}
}
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Begunov, Roman Sergeevich, et al. “Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 633-635. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.027.

Keywords

cyclic voltammetry
electrochemical reduction
heterocyclization
nitroarenes
piperidines
pyrido[1,2-a]benzimidazoles
pyrido[3′,2′:4,5]imidazo[1,2-a]pyridines

Abstract

Electrochemical reduction of ortho-piperidino substituted nitro(het)arenes in an undivided cell on a lead cathode in 8% HCl gave either 1,2,3,4-tetrahydropyrido[1,2-a]-benzimidazoles or 6,7,8,9-tetrahydropyrido[3′,2′:4,5]- imidazo[1,2-a]pyridines. The reductive heterocyclization mechanism involves the initial formation of a nitroso derivative followed by the formation of an imidazole ring.

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