ChemistrySelect.
Wiley-Blackwell.
Vol. 3.
2018.
P. 3107-3110
First example of the cascade acylation/IMDAV/ene reaction sequence, leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity
The reaction between readily accessible N-aryl-3-phenylallylamines and maleic anhydride led to unexpected products – polysubstituted hydrogenated benzo[f]isoindole-4-carboxylic acids. This transformation proceeds through a previously unknown sequence of steps: N-acylation of the allylamine with maleic anhydride, intramolecular Diels-Alder reaction of the vinylarene in the intermediate N-maleamide, and Alder-ene reaction of the products of the previous two steps. Selected benzo[f]isoindoles displayed antiviral activity. © 2018 Elsevier Ltd
Authors
Voronov A.A.
1
,
Alekseeva K.A.
1
,
Ryzhkova E.A.
1
,
Zarubaev V.V.2
,
Galochkina A.V.3
,
Zaytsev V.P.
1
,
Majik M.S.4
,
Tilve S.G.
4
,
Gurbanov A.V.
5,
6
,
Zubkov F.I.
1
Journal
Publisher
Elsevier Ltd
Number of issue
12
Language
English
Pages
1108-1111
Status
Published
Link
Volume
59
Year
2018
Organizations
- 1 Department of Organic Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
- 2 Pasteur Institute of Epidemiology and Microbiology, 14 Mira St., St. Petersburg, 197101, Russian Federation
- 3 Department of Pre-clinical Trials, Influenza Research Institute, 15/17 Prof. Popova St., St. Petersburg, 197376, Russian Federation
- 4 Department of Chemistry, Goa University, Taleigao PlateauGoa 403 206, India
- 5 Department of Organic Chemistry, Baku State University, Z. Khalilov str. 23, Baku, AZ 1148, Azerbaijan
- 6 Centro de QuímicaEstrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. RoviscoPais, Lisbon, 1049-001, Portugal
Keywords
Alder-ene reaction; Anti-viral activity; Benzo[f]isoindoles; IMDAV reaction; [4+2] cycloaddition
Date of creation
19.10.2018
Date of change
12.08.2021
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MATEC Web of Conferences.
EDP Sciences.
Vol. 158.
2018.