Four-component stereoselective synthesis of tetracyano-substituted piperidines
Publication type: Journal Article
Publication date: 2018-04-25
scimago Q2
wos Q2
SJR: 0.528
CiteScore: 5.7
Impact factor: 3.5
ISSN: 09226168, 15685675
General Chemistry
Abstract
A novel four-component stereoselective synthesis of polysubstituted piperidines is reported. The Knoevenagel–Michael–Mannich cascade of two equivalents of aromatic aldehydes, formaldehyde, two equivalents of malononitrile and ammonium acetate provides convenient access to the 2,6-diaryl-3,3,5,5-tetracyanopiperidines in good to excellent yields. Ammonium acetate plays a role both as a catalyst and as a nitrogen source. The formation of products is highly stereoselective. Structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, IR, elemental analysis and mass spectral studies. 2,6-diphenylpiperidine-3,3,5,5-tetracarbonitrile was characterized by X-ray diffraction.
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Total citations:
17
Citations from 2025:
1
(5.88%)
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GOST
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Vereshchagin A. N. et al. Four-component stereoselective synthesis of tetracyano-substituted piperidines // Research on Chemical Intermediates. 2018. Vol. 44. No. 9. pp. 5623-5634.
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Vereshchagin A. N., Karpenko K. A., Elinson M. N., Goloveshkin A. S., Ushakov I. E., Egorov M. P. Four-component stereoselective synthesis of tetracyano-substituted piperidines // Research on Chemical Intermediates. 2018. Vol. 44. No. 9. pp. 5623-5634.
Cite this
RIS
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TY - JOUR
DO - 10.1007/s11164-018-3444-7
UR - https://link.springer.com/10.1007/s11164-018-3444-7
TI - Four-component stereoselective synthesis of tetracyano-substituted piperidines
T2 - Research on Chemical Intermediates
AU - Vereshchagin, Anatoly N.
AU - Karpenko, Kirill A
AU - Elinson, Michail N
AU - Goloveshkin, Alexander S.
AU - Ushakov, Ivan E.
AU - Egorov, Mikhail P.
PY - 2018
DA - 2018/04/25
PB - Springer Nature
SP - 5623-5634
IS - 9
VL - 44
SN - 0922-6168
SN - 1568-5675
ER -
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BibTex (up to 50 authors)
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@article{2018_Vereshchagin,
author = {Anatoly N. Vereshchagin and Kirill A Karpenko and Michail N Elinson and Alexander S. Goloveshkin and Ivan E. Ushakov and Mikhail P. Egorov},
title = {Four-component stereoselective synthesis of tetracyano-substituted piperidines},
journal = {Research on Chemical Intermediates},
year = {2018},
volume = {44},
publisher = {Springer Nature},
month = {apr},
url = {https://link.springer.com/10.1007/s11164-018-3444-7},
number = {9},
pages = {5623--5634},
doi = {10.1007/s11164-018-3444-7}
}
Cite this
MLA
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Vereshchagin, Anatoly N., et al. “Four-component stereoselective synthesis of tetracyano-substituted piperidines.” Research on Chemical Intermediates, vol. 44, no. 9, Apr. 2018, pp. 5623-5634. https://link.springer.com/10.1007/s11164-018-3444-7.