First example of the cascade acylation/IMDAV/ene reaction sequence, leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity. Issue 12 (21st March 2018)

• Record Type: Journal Article
• Authors: Voronov, Alexander A.; Alekseeva, Kseniia A.; Ryzhkova, Elena A.; Zarubaev, Vladimir V.; Galochkina, Anastasia V.; Zaytsev, Vladimir P.; Majik, Mahesh S.; Tilve, Santosh G.; Gurbanov, Atash V.; Zubkov, Fedor I.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 12(2018)
• Page Start: 1108
• Page End: 1111
• Publication Date: 2018-03-21
• Subjects: IMDAV reaction -- Alder-ene reaction -- Benzo[f]isoindoles -- Anti-viral activity -- [4+2] cycloaddition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.02.015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: One-step and diastereoselective approach for benzo[ f ]isoindole-4-carboxylic acids. Previously unknown tandem N -acylation/IMDAV/Alder-ene reaction was discovered. Benzo[ f ]isoindoles display antiviral activity against the influenza virus H1N1. 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.