Domino Three-Component N-Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[f]isoindole-4-carboxylic Acids
Maryana A. Nadirova
1
,
M A Nadirova
1
,
Evgeniya V. Nikitina
1
,
Anton P. Novikov
1, 2
,
Irina A. Kolesnik
3
,
Bernhard Mayer
4
,
Bernd Mayer
4
,
TJ Müller
4
,
Publication type: Journal Article
Publication date: 2023-10-23
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
37870950
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.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
|
|
|
Organic and Biomolecular Chemistry
3 publications, 50%
|
|
|
Organic Letters
1 publication, 16.67%
|
|
|
Acta Crystallographica Section E: Crystallographic Communications
1 publication, 16.67%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 16.67%
|
|
|
1
2
3
|
Publishers
|
1
2
3
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 50%
|
|
|
American Chemical Society (ACS)
1 publication, 16.67%
|
|
|
International Union of Crystallography (IUCr)
1 publication, 16.67%
|
|
|
Wiley
1 publication, 16.67%
|
|
|
1
2
3
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
6
Total citations:
6
Citations from 2024:
6
(100%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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.
Cite this
RIS
Copy
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 -
Cite this
BibTex (up to 50 authors)
Copy
@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}
}
Cite this
MLA
Copy
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.