A. P. Krinochkin, E. S. Starnovskaya, M. I. Valieva, D. S. Kopchuk, S. Santra, P. A. Slepukhin, G. V. Zyryanov, A. Majee, O. N. Chupakhin, “One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions”, Mendeleev Commun., 2022, Volume 32, Issue 4,Pages 449

This article is cited in 4 papers

Communications

One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/S_N^ipso reactions

A. P. Krinochkin^ab, E. S. Starnovskaya^ab, M. I. Valieva^ab, D. S. Kopchuk^ab, S. Santra^b, P. A. Slepukhin^ab, G. V. Zyryanov^ab, A. Majee^c, O. N. Chupakhin^ab

^a I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation
^c Department of Chemistry, Visva-Bharati University, Santiniketan, West Bengal, India

Abstract: One-pot synthesis of cyclopentane-fused 5'-aryl-4- cycloalkylamino-2,2'-bipyridines based on the neat (200 °C) reaction of 3-(4-bromopyridin-2-yl)-1,2,4-triazines with enamines is reported. In the course of the transformation, consecutive aza-Diels–Alder reaction and nucleophilic substitution of bromine atom under the action of the liberating amine occur. The possibility of the solvent- and catalyst-free replacement of 4-positioned bromine atom in 2,2'-bipyridines by amino moieties was demonstrated.

Keywords: amino-2, 2'-bipyridines, 124-triazines, aza-Diels–Alder reaction, ipso-substitution, solvent-free reaction, one-pot synthesis, enamines.

Language: English

DOI: 10.1016/j.mencom.2022.07.007

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