R. S. Begunov, V. O. Sakulina, M. A. Syroeshkin, E. A. Saverina, A. A. Sokolov, M. E. Minyaev, “Electroreductive heterocyclization of <i>ortho</i>-piperidino substituted nitro(het)arenes”, Mendeleev Commun., 2020, Volume 30, Issue 5,Pages <nobr>633

This article is cited in 7 papers

Communications

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

R. S. Begunov^a, V. O. Sakulina^a, M. A. Syroeshkin^b, E. A. Saverina^b, A. A. Sokolov^a, M. E. Minyaev^b

^a P.G. Demidov Yaroslavl State University, Yaroslavl, Russian Federation
^b N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

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.

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

Language: English

DOI: 10.1016/j.mencom.2020.09.027

	*Supplementary materials:*
		Supplementary_data_1.pdf	1.1 Mb