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First example of the cascade acylation/IMDAV/ene reaction sequence,leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity |
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| Authors: | Alexander A. Voronov Kseniia A. Alekseeva Elena A. Ryzhkova Vladimir V. Zarubaev Anastasia V. Galochkina Vladimir P. Zaytsev Mahesh S. Majik Santosh G. Tilve Atash V. Gurbanov Fedor I. Zubkov |
| Affiliation: | 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., 197101 St. Petersburg, Russian Federation;3. Department of Pre-clinical Trials, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russian Federation;4. Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India;5. Department of Organic Chemistry, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan;6. Centro de QuímicaEstrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. RoviscoPais, 1049-001 Lisbon, Portugal |
| 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. |
| Keywords: | IMDAV reaction Alder-ene reaction Anti-viral activity [4+2] cycloaddition |
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