Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines
Publication type: Journal Article
Publication date: 2021-09-30
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
A novel four-component diastereoselective synthesis of polysubstituted tetrahydropyridines is reported. The Michael addition – Mannich reaction – cyclization – dehydration cascade of benzylidenemalononitriles, esters of 3-oxocarboxylic acids, aromatic aldehydes, and ammonium acetate in methanol provides convenient access to 2-substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridine- 3-carboxylates with two stereocenters in 66–92% yields. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays dual role acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by 1H, 13C NMR, IR, and mass spectral studies. The formation of single diastereomer was confirmed by singe crystal X-ray diffraction studies.
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Total citations:
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Citations from 2025:
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Vereshchagin A. N. et al. Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 9. pp. 929-933.
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Vereshchagin A. N., Iliyasov T. M., Karpenko K. A., Smirnov V. A., Ushakov I. E., Elinson M. N. Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 9. pp. 929-933.
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TY - JOUR
DO - 10.1007/s10593-021-03002-5
UR - https://link.springer.com/10.1007/s10593-021-03002-5
TI - Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines
T2 - Chemistry of Heterocyclic Compounds
AU - Vereshchagin, Anatoly N.
AU - Iliyasov, Taygib M
AU - Karpenko, Kirill A
AU - Smirnov, Vladimir A.
AU - Ushakov, Ivan E.
AU - Elinson, Michail N
PY - 2021
DA - 2021/09/30
PB - Springer Nature
SP - 929-933
IS - 9
VL - 57
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2021_Vereshchagin,
author = {Anatoly N. Vereshchagin and Taygib M Iliyasov and Kirill A Karpenko and Vladimir A. Smirnov and Ivan E. Ushakov and Michail N Elinson},
title = {Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines},
journal = {Chemistry of Heterocyclic Compounds},
year = {2021},
volume = {57},
publisher = {Springer Nature},
month = {sep},
url = {https://link.springer.com/10.1007/s10593-021-03002-5},
number = {9},
pages = {929--933},
doi = {10.1007/s10593-021-03002-5}
}
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MLA
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Vereshchagin, Anatoly N., et al. “Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines.” Chemistry of Heterocyclic Compounds, vol. 57, no. 9, Sep. 2021, pp. 929-933. https://link.springer.com/10.1007/s10593-021-03002-5.