volume 44 issue 9 pages 5623-5634

Four-component stereoselective synthesis of tetracyano-substituted piperidines

Publication typeJournal Article
Publication date2018-04-25
scimago Q2
wos Q2
SJR0.528
CiteScore5.7
Impact factor3.5
ISSN09226168, 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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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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MLA Copy
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.