Open Access
Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones
E.V. Suslov
1
,
Konstantin Y Ponomarev
1
,
Oxana S Patrusheva
1
,
Sergey O Kuranov
1
,
Alina A Okhina
1, 2
,
Artem Rogachev
1, 2
,
Aldar A Munkuev
1
,
Roman V Ottenbacher
3
,
Alexander I Dalinger
4
,
Nariman F. Salakhutdinov
1
Publication type: Journal Article
Publication date: 2021-12-13
PubMed ID:
34946622
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
A number of new chiral bispidines containing monoterpenoid fragments have been obtained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed, in which the peaks of the enantiomers of all synthesized chiral products were separated, which made it possible to determine the enantiomeric excess of the resulting mixture. It was demonstrated that bispidine-monoterpenoid conjugates can be used as the ligands for diethylzinc addition to chalcone C=C double bond but not as inducers of chirality. Besides products of ethylation, formation of products of formal hydrogenation of the chalcone C=C double bond was observed in all cases. Note, that this formation of hydrogenation products in significant amounts in the presence of such catalytic systems was found for the first time. A tentative scheme explaining the formation of all products was proposed.
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15
Total citations:
15
Citations from 2024:
10
(66%)
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MLA
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GOST
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Suslov E. et al. Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones // Molecules. 2021. Vol. 26. No. 24. p. 7539.
GOST all authors (up to 50)
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Suslov E., Ponomarev K. Y., Patrusheva O. S., Kuranov S. O., Okhina A. A., Rogachev A., Munkuev A. A., Ottenbacher R. V., Dalinger A. I., Kalinin M. A., Vatsadze S. Z., Volcho K. P., Salakhutdinov N. F. Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones // Molecules. 2021. Vol. 26. No. 24. p. 7539.
Cite this
RIS
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TY - JOUR
DO - 10.3390/molecules26247539
UR - https://www.mdpi.com/1420-3049/26/24/7539
TI - Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones
T2 - Molecules
AU - Suslov, E.V.
AU - Ponomarev, Konstantin Y
AU - Patrusheva, Oxana S
AU - Kuranov, Sergey O
AU - Okhina, Alina A
AU - Rogachev, Artem
AU - Munkuev, Aldar A
AU - Ottenbacher, Roman V
AU - Dalinger, Alexander I
AU - Kalinin, Mikhail A
AU - Vatsadze, Sergey Z.
AU - Volcho, Konstantin P.
AU - Salakhutdinov, Nariman F.
PY - 2021
DA - 2021/12/13
PB - MDPI
SP - 7539
IS - 24
VL - 26
PMID - 34946622
SN - 1420-3049
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Suslov,
author = {E.V. Suslov and Konstantin Y Ponomarev and Oxana S Patrusheva and Sergey O Kuranov and Alina A Okhina and Artem Rogachev and Aldar A Munkuev and Roman V Ottenbacher and Alexander I Dalinger and Mikhail A Kalinin and Sergey Z. Vatsadze and Konstantin P. Volcho and Nariman F. Salakhutdinov},
title = {Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {MDPI},
month = {dec},
url = {https://www.mdpi.com/1420-3049/26/24/7539},
number = {24},
pages = {7539},
doi = {10.3390/molecules26247539}
}
Cite this
MLA
Copy
Suslov, E.V., et al. “Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones.” Molecules, vol. 26, no. 24, Dec. 2021, p. 7539. https://www.mdpi.com/1420-3049/26/24/7539.