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.
Citation:
R. S. Begunov, V. O. Sakulina, M. A. Syroeshkin, E. A. Saverina, A. A. Sokolov, M. E. Minyaev, “Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes”, Mendeleev Commun., 30:5 (2020), 633–635
Linking options:
https://www.mathnet.ru/eng/mendc1276
https://www.mathnet.ru/eng/mendc/v30/i5/p633
This publication is cited in the following 7 articles:
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Haoran Zhu, Jair N. Powell, Victoria A. Geldchen, Adam S. Drumheller, Tom G. Driver, “Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline N‐Oxides by Electrochemical Reductive Cyclization”, Angew Chem Int Ed, 2024
Haoran Zhu, Jair N. Powell, Victoria A. Geldchen, Adam S. Drumheller, Tom G. Driver, “Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline N‐Oxides by Electrochemical Reductive Cyclization”, Angewandte Chemie, 2024
Dong Zou, Wei Wang, Yaqin Hu, Tingting Jia, “Nitroarenes and nitroalkenes as potential amino sources for the synthesis of N-heterocycles”, Org. Biomol. Chem., 21:11 (2023), 2254
Haoran Zhu, Tom G. Driver, “Recent Advances to Mediate Reductive Processes of Nitroarenes Using Single-Electron Transfer, Organomagnesium, or Organozinc Reagents”, Synthesis, 54:14 (2022), 3142
R. S. Begunov, Yu. V. Zaitseva, A. A. Sokolov, D. O. Egorov, S. I. Filimonov, “Synthesis and Antibacterial Activity of 1,2,3,4-Tetrahydro- and Pyrido[1,2-a]Benzimidazoles”, Pharm Chem J, 56:1 (2022), 22
Martin Sweeney, Darren Conboy, Styliana I. Mirallai, Fawaz Aldabbagh, “Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles”, Molecules, 26:9 (2021), 2684
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