Journal of Organic Chemistry, volume 88, issue 21, pages 15029-15040
Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids
Nadirova Maryana A.
1
,
Nikitina Evgeniya V.
1
,
Grigoriev Mikhail S.
2
,
Novikov Anton P.
1, 2
,
Kolesnik Irina A.
3
,
Mayer Bernhard
4
,
Müller TJ
4
,
4
Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany
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Publication type: Journal Article
Publication date: 2023-10-23
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
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.
Citations by journals
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Organic and Biomolecular Chemistry
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Organic and Biomolecular Chemistry
1 publication, 100%
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1
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Citations by publishers
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1
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 100%
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1
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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., Zaytsev V. P., Nikitina E. V., Grigoriev M. S., Novikov A. P., Kolesnik I. A., 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://doi.org/10.1021%2Facs.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 - Zaytsev, Vladimir P.
AU - Nikitina, Evgeniya V.
AU - Grigoriev, Mikhail S.
AU - Novikov, Anton P.
AU - Kolesnik, Irina A.
AU - Mayer, Bernhard
AU - Müller, TJ
AU - Zubkov, Fedor I.
PY - 2023
DA - 2023/10/23 00:00:00
PB - American Chemical Society (ACS)
SP - 15029-15040
IS - 21
VL - 88
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Alekseeva,
author = {Kseniya A. Alekseeva and Maryana A. Nadirova and Vladimir P. Zaytsev and Evgeniya V. Nikitina and Mikhail S. Grigoriev and Anton P. Novikov and Irina A. Kolesnik and Bernhard 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://doi.org/10.1021%2Facs.joc.3c01476},
number = {21},
pages = {15029--15040},
doi = {10.1021/acs.joc.3c01476}
}
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MLA
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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://doi.org/10.1021%2Facs.joc.3c01476.