Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids
Б. А. ТрофимовA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian FederationLudmila V. AndriyankovaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian FederationRustem T. TlegenovDepartment of Chemistry, Karakalpak State University, 742012 Nukus, UzbekistanAnastasiya G. Mal’kinaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian FederationА. В. АфонинA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian FederationL. N. Il’ichevaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian FederationLina P. NikitinaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
ABI
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.
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