Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton
Publication type: Journal Article
Publication date: 2020-06-10
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32517470
Organic Chemistry
Abstract
The one-pot regio- and diastereoselective method for the synthesis of 5-(het)aroyl-7-(het)arylhexahydrobenzo[4,5]pentaleno[1,6a-b](thia)pyrrolizine-6,12-diones from accessible 1,5-di(het)arylpent-4-ene-1,3-diones or curcuminoids in 38-98% yields was developed. This reaction proceeds as a sequence of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from ninhydrin and (thia)proline at the C=C bond of corresponding enedione, followed by spontaneous intramolecular aldol condensation and leads to the formation of an azatetraquinane scaffold.
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12
Total citations:
12
Citations from 2024:
4
(33%)
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GOST
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Zimnitskiy N. S. et al. Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton // Journal of Organic Chemistry. 2020. Vol. 85. No. 13. pp. 8683-8694.
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Zimnitskiy N. S., Denikaev A., Barkov A. V., Kutyashev I., Korotaev V. Y., Sosnovskikh V. Y. Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton // Journal of Organic Chemistry. 2020. Vol. 85. No. 13. pp. 8683-8694.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.0c01127
UR - https://doi.org/10.1021/acs.joc.0c01127
TI - Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton
T2 - Journal of Organic Chemistry
AU - Zimnitskiy, Nikolay S
AU - Denikaev, Andrey
AU - Barkov, Alexey V.
AU - Kutyashev, I.
AU - Korotaev, Vladislav Y
AU - Sosnovskikh, Vyacheslav Ya.
PY - 2020
DA - 2020/06/10
PB - American Chemical Society (ACS)
SP - 8683-8694
IS - 13
VL - 85
PMID - 32517470
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2020_Zimnitskiy,
author = {Nikolay S Zimnitskiy and Andrey Denikaev and Alexey V. Barkov and I. Kutyashev and Vladislav Y Korotaev and Vyacheslav Ya. Sosnovskikh},
title = {Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.0c01127},
number = {13},
pages = {8683--8694},
doi = {10.1021/acs.joc.0c01127}
}
Cite this
MLA
Copy
Zimnitskiy, Nikolay S., et al. “Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton.” Journal of Organic Chemistry, vol. 85, no. 13, Jun. 2020, pp. 8683-8694. https://doi.org/10.1021/acs.joc.0c01127.