One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions |
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| Institution: | 1. Institute of Chemical Engineering, Ural Federal University, 620002 Ekaterinburg, Russian Federation;2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620990 Ekaterinburg, Russian Federation;3. Department of Chemistry, Visva-Bharati (A Central University), 731235 Santiniketan, India |
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| 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. |
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| Keywords: | amino-2 124-triazines solvent-free reaction one-pot synthesis enamines |
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