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

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
, 
Ludmila Viktorovna Andriyankova 1
Ludmila Viktorovna Andriyankova
, 
Rustem Tolegenovich Tlegenov 2
Rustem Tolegenovich Tlegenov
, 
Anastasiya Grigor'evna Mal'kina 1
Anastasiya Grigor'evna Mal'kina
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Lubov Nikolaevna Il'icheva 1
Lubov Nikolaevna Il'icheva
, 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
10.1070/MC2005v015n01ABEH001904
Published 2005-02-09
Communication , Volume 15, Issue 1, 33-35
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Trofimov B. A. et al. Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids // Mendeleev Communications. 2005. Vol. 15. No. 1. pp. 33-35.
GOST all authors (up to 50) Copy
Trofimov B. A., Andriyankova L. V., Tlegenov R. T., Mal'kina A. G., Afonin A. V., Il'icheva L. N., Nikitina L. P. Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids // Mendeleev Communications. 2005. Vol. 15. No. 1. pp. 33-35.
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TY - JOUR
DO - 10.1070/MC2005v015n01ABEH001904
UR - https://mendcomm.colab.ws/publications/10.1070/MC2005v015n01ABEH001904
TI - Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Andriyankova, Ludmila Viktorovna
AU - Tlegenov, Rustem Tolegenovich
AU - Mal'kina, Anastasiya Grigor'evna
AU - Afonin, Andrei Valer'evich
AU - Il'icheva, Lubov Nikolaevna
AU - Nikitina, Lina Pavlovna
PY - 2005
DA - 2005/02/09
PB - Mendeleev Communications
SP - 33-35
IS - 1
VL - 15
ER -
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@article{2005_Trofimov,
author = {Boris Aleksandrovich Trofimov and Ludmila Viktorovna Andriyankova and Rustem Tolegenovich Tlegenov and Anastasiya Grigor'evna Mal'kina and Andrei Valer'evich Afonin and Lubov Nikolaevna Il'icheva and Lina Pavlovna Nikitina},
title = {Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids},
journal = {Mendeleev Communications},
year = {2005},
volume = {15},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2005v015n01ABEH001904},
number = {1},
pages = {33--35},
doi = {10.1070/MC2005v015n01ABEH001904}
}
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Trofimov, Boris Aleksandrovich, et al. “Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids.” Mendeleev Communications, vol. 15, no. 1, Feb. 2005, pp. 33-35. https://mendcomm.colab.ws/publications/10.1070/MC2005v015n01ABEH001904.

Abstract

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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