Open Access
Molecules, volume 28, issue 1, pages 88
Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors
Publication type: Journal Article
Publication date: 2022-12-22
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
Quinolizidine and azaphenalene alkaloids are common in nature and exhibit a pharmaceutical activity, which stirs up increased interest in expanding the range of methods for the synthesis of the corresponding derivatives. In this work, we attempted to adapt our previously presented method for the synthesis of tetrahydropyridines to the preparation of potential precursors for these heterocycles as a separate development of a necessary intermediate stage. To this end, we studied the reactions of β-styrylmalonates with N-protected cross-conjugated azatrienes in the presence of Sn(OTf)2. Moreover, the regioselectivity of the process involving unsymmetrically substituted azatrienes was estimated. The diene character of vinyltetrahydropyridines was studied in detail with the participation of PTAD. Finally, for the Ts-protected highly functionalized vinyltetrahydropyridines synthesized, a detosylation method to give new desired azadiene structures as precursors of the quinolizidine core was suggested.
Top-30
Citations by journals
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Russian Journal of Organic Chemistry
1 publication, 33.33%
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Russian Chemical Reviews
1 publication, 33.33%
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Journal of Molecular Graphics and Modelling
1 publication, 33.33%
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Citations by publishers
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Pleiades Publishing
1 publication, 33.33%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 33.33%
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Elsevier
1 publication, 33.33%
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- We do not take into account publications without a DOI.
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Sergeev P. G., Novikov R. A., Tomilov Y. V. Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors // Molecules. 2022. Vol. 28. No. 1. p. 88.
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Sergeev P. G., Novikov R. A., Tomilov Y. V. Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors // Molecules. 2022. Vol. 28. No. 1. p. 88.
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TY - JOUR
DO - 10.3390/molecules28010088
UR - https://doi.org/10.3390/molecules28010088
TI - Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors
T2 - Molecules
AU - Sergeev, Pavel G
AU - Novikov, Roman A
AU - Tomilov, Yury V.
PY - 2022
DA - 2022/12/22 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 88
IS - 1
VL - 28
SN - 1420-3049
SN - 1420-3049
ER -
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@article{2022_Sergeev,
author = {Pavel G Sergeev and Roman A Novikov and Yury V. Tomilov},
title = {Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors},
journal = {Molecules},
year = {2022},
volume = {28},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {dec},
url = {https://doi.org/10.3390/molecules28010088},
number = {1},
pages = {88},
doi = {10.3390/molecules28010088}
}
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Sergeev, Pavel G., et al. “Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors.” Molecules, vol. 28, no. 1, Dec. 2022, p. 88. https://doi.org/10.3390/molecules28010088.
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