Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids
Тип публикации: Journal Article
Дата публикации: 2023-10-23
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
37870950
Organic Chemistry
Краткое описание
Diversely substituted, partially saturated benzo[f]isoindole-4-carboxylic acids were synthesized by a new three-component reaction (3CR) starting from cinnamic amines (3-arylallylamines), maleimides, and maleic anhydride. The process consists of N-acylation of the amines by maleic anhydride, intramolecular [4 + 2] cycloaddition in vinylarenes (the IMDAV reaction), and the concluding Alder-ene reaction between Diels–Alder intermediates and maleimides. All of the reaction steps proceed in a highly regio- and stereoselective manner, furnishing five adjacent chiral centers and leading to a single diastereoisomer of the title compound. The efficiency of the transformation is secured by thermal conditions or utilization of soft Lewis acids (Yb(OTf)3) as catalysts. The kinetics and mechanism of the 3CR were studied by using dynamic 19F NMR. Based on the NMR data and density functional theory (DFT) calculations, the IMDAV, not the Alder-ene, reaction is the rate-limiting step of the entire process.
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Alekseeva K. A. et al. Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids // Journal of Organic Chemistry. 2023. Vol. 88. No. 21. pp. 15029-15040.
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Alekseeva K. A., Nadirova M. A., Nadirova M. A., Zaytsev V. P., Nikitina E. V., Nikitina E. V., Grigoriev M. S., Novikov A. P., Kolesnik I. A., Mayer B., Mayer B., Müller T., Zubkov F. I. Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids // Journal of Organic Chemistry. 2023. Vol. 88. No. 21. pp. 15029-15040.
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TY - JOUR
DO - 10.1021/acs.joc.3c01476
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c01476
TI - Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids
T2 - Journal of Organic Chemistry
AU - Alekseeva, Kseniya A.
AU - Nadirova, Maryana A.
AU - Nadirova, M A
AU - Zaytsev, Vladimir P.
AU - Nikitina, Evgeniya V.
AU - Nikitina, Eugeniya V.
AU - Grigoriev, Mikhail S.
AU - Novikov, Anton P.
AU - Kolesnik, Irina A.
AU - Mayer, Bernhard
AU - Mayer, Bernd
AU - Müller, TJ
AU - Zubkov, Fedor I.
PY - 2023
DA - 2023/10/23
PB - American Chemical Society (ACS)
SP - 15029-15040
IS - 21
VL - 88
PMID - 37870950
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Alekseeva,
author = {Kseniya A. Alekseeva and Maryana A. Nadirova and M A Nadirova and Vladimir P. Zaytsev and Evgeniya V. Nikitina and Eugeniya V. Nikitina and Mikhail S. Grigoriev and Anton P. Novikov and Irina A. Kolesnik and Bernhard Mayer and Bernd Mayer and TJ Müller and Fedor I. Zubkov},
title = {Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c01476},
number = {21},
pages = {15029--15040},
doi = {10.1021/acs.joc.3c01476}
}
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Alekseeva, Kseniya A., et al. “Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids.” Journal of Organic Chemistry, vol. 88, no. 21, Oct. 2023, pp. 15029-15040. https://pubs.acs.org/doi/10.1021/acs.joc.3c01476.
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