B. A. Trofimov, L. V. Andriyankova, R. T. Tlegenov, A. G. Mal'kina, A. V. Afonin, L. N. Il'icheva, L. P. Nikitina, “Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids”, Mendeleev Commun., 15:1 (2005), 33

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Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids

B. A. Trofimov^a, L. V. Andriyankova^a, R. T. Tlegenov^b, A. G. Mal'kina^a, A. V. Afonin^a, L. N. Il'icheva^a, L. P. Nikitina^a

^a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
^b Department of Chemistry, Karakalpak State University, Nukus, Uzbekistan

Аннотация: Chemo- and regioselective addition of anabasine to 3-(1-hydroxycyclohexyl)-2-propynenitrile in ethanol results in 52% yield of a monoadduct, (Z)-3-(1-hydroxycyclohexyl)-3-[2-(3-pyridinyl)piperidino]-2-propenenitrile: in this case, only the piperidine ring of anabasine takes part in the reaction. In acetonitrile, both piperidine and pyridine rings participate in the process giving a diadduct, (Z)-3-{2-[3-[(Z)-cyanomethylidene]-2-spirocyclohexyl-8aH-[1,3]oxazolo[3,2-a]pyridine-8(2H)-yl]piperidino}-3-(1-hydroxycyclohexyl)-2-propenenitrile in 68% yield.

Язык публикации: английский

DOI: 10.1070/MC2005v015n01ABEH001904