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Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines

Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
, 
Kirill Anatol'evich Karpenko 1
Kirill Anatol'evich Karpenko
,  , 
Evgeniya Olegovna Dorofeeva 1
Evgeniya Olegovna Dorofeeva
, 
Alexander Sergeyevich Goloveshkin 2
Alexander Sergeyevich Goloveshkin
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
10.1016/j.mencom.2018.07.014
Published 2018-06-29
Communication , Volume 28, Issue 4, 384-386
16
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Vereshchagin A. N. et al. Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines // Mendeleev Communications. 2018. Vol. 28. No. 4. pp. 384-386.
GOST all authors (up to 50) Copy
Vereshchagin A. N., Karpenko K. A., Elinson M. N., Dorofeeva E. O., Goloveshkin A. S., Egorov M. P. Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines // Mendeleev Communications. 2018. Vol. 28. No. 4. pp. 384-386.
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TY - JOUR
DO - 10.1016/j.mencom.2018.07.014
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.07.014
TI - Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines
T2 - Mendeleev Communications
AU - Vereshchagin, Anatoly Nikolaevich
AU - Karpenko, Kirill Anatol'evich
AU - Elinson, Michail Nikolaevich
AU - Dorofeeva, Evgeniya Olegovna
AU - Goloveshkin, Alexander Sergeyevich
AU - Egorov, Mikhail Petrovich
PY - 2018
DA - 2018/06/29
PB - Mendeleev Communications
SP - 384-386
IS - 4
VL - 28
ER -
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@article{2018_Vereshchagin,
author = {Anatoly Nikolaevich Vereshchagin and Kirill Anatol'evich Karpenko and Michail Nikolaevich Elinson and Evgeniya Olegovna Dorofeeva and Alexander Sergeyevich Goloveshkin and Mikhail Petrovich Egorov},
title = {Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.07.014},
number = {4},
pages = {384--386},
doi = {10.1016/j.mencom.2018.07.014}
}
MLA
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Vereshchagin, Anatoly Nikolaevich, et al. “Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines.” Mendeleev Communications, vol. 28, no. 4, Jun. 2018, pp. 384-386. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.07.014.

Abstract

The Knövenagel–Michael–Mannich cascade reaction of aromatic aldehyde (3 equiv.), malononitrile (2 equiv.) and ammonium acetate or aqueous ammonia provides convenient stereoselective access to cis,cis-2,4,6-triaryl-3,3,5,5-tetracyanopiperidines in 62–94% yields. Six new bonds form as a result of the domino process, ammonium acetate serving as a nitrogen source.

References

3.
Ananikov V.P., Galkin K.I., Egorov M.P., Sakharov A.M., Zlotin S.G., Redina E.A., Isaeva V.I., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications, 2016
7.
D. A. Elbein and R. Molyneux, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Palletier, Wiley, New York, 1987, vol. 5, pp. 1-54.
8.
Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives
Weis R., Schweiger K., Faist J., Rajkovic E., Kungl A.J., Fabian W.M., Schunack W., Seebacher W.
Bioorganic and Medicinal Chemistry, 2008
10.
Synthesis of Polysubstituted 2-Piperidinones via a Michael Addition/Nitro-Mannich/Lactamization Cascade
Liu H., Zhou Z., Sun Q., Li Y., Li Y., Liu J., Yan P., Wang D., Wang C.
ACS Combinatorial Science, 2012
11.
Electrochemically induced Favorsky rearrangement of alkyl benzyl ketones
Elinson M.N., Feducovich S.K., Dorofeev A.S., Vereshchagin A.N., Nikishin G.I.
Russian Chemical Bulletin, 2003
15.
Electrochemically induced Favorsky rearrangement: transformations of dialkyl ketones into α,β-unsaturated carboxylic esters
Elinson M.N., Feducovich S.K., Zaimovskaya T.A., Dorofeev A.S., Vereshchagin A.N., Nikishin G.I.
Russian Chemical Bulletin, 2003
17.
Multicomponent assembling of salicylaldehydes, malononitrile, and 4-hydroxy-6-methyl-2H-pyran-2-one: A fast and efficient approach to medicinally relevant 2-amino-4H-chromene scaffold
Vereshchagin A.N., Elinson M.N., Ryzhkov F.V., Nasybullin R.F., Bobrovsky S.I., Goloveshkin A.S., Egorov M.P.
Comptes Rendus Chimie, 2015
19.
PASE Pseudo-Four-Component Synthesis and Docking Studies of New 5-C-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]pyridine-3-Carbonitriles
Vereshchagin A.N., Elinson M.N., Anisina Y.E., Ryzhkov F.V., Novikov R.A., Egorov M.P.
ChemistrySelect, 2017
20.
One-Pot ‘On-solvent’ Multicomponent Protocol for the Synthesis of Medicinally Relevant 4H-Pyrano[3,2-c]quinoline Scaffold
Vereshchagin A.N., Elinson M.N., Nasybullin R.F., Ryzhkov F.V., Bobrovsky S.I., Bushmarinov I.S., Egorov M.P.
Helvetica Chimica Acta, 2015
22.
Electrophilicity Parameters for Benzylidenemalononitriles
Lemek T., Mayr H.
Journal of Organic Chemistry, 2003
24.
A new type of cascade reaction: direct conversion of carbonyl compounds and malononitrile into substituted tetracyanocyclopropanes
Elinson M.N., Vereshchagin A.N., Stepanov N.O., Ilovaisky A.I., Vorontsov A.Y., Nikishin G.I.
Tetrahedron, 2009