First example of the cascade acylation/IMDAV/ene reaction sequence, leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity

Voronov, A.A.; Alekseeva, K.A.; Ryzhkova, E.A.; Zarubaev, V.V.; Galochkina, A.V.; Zaytsev, V.P.; Majik, M.S.; Tilve, S.G.; Gurbanov, A.V.; Zubkov, F.I.

First example of the cascade acylation/IMDAV/ene reaction sequence, leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity

Voronov, A.A.; Alekseeva, K.A.; Ryzhkova, E.A.; Zarubaev, V.V.; Galochkina, A.V.; Zaytsev, V.P.; Majik, M.S.; Tilve, S.G.; Gurbanov, A.V.; Zubkov, F.I.

Source : Tetrahedron Letters. 59(12); 2018; 1108-1111.

URI: https://doi.org/10.1016/j.tetlet.2018.02.015
http://irgu.unigoa.ac.in/drs/handle/unigoa/5110

Date: 2018

Document Type: Journal article

Abstract:

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.

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