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

Авторы
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
Журнал
Tetrahedron Letters
Издательство
Elsevier Ltd
Номер выпуска
12
Язык
Английский
Страницы
1108-1111
Статус
Опубликовано
Ссылка
Внешняя ссылка
DOI
10.1016/J.TETLET.2018.02.015
Том
59
Год
2018
Организации
  • 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
Ключевые слова
Alder-ene reaction; Anti-viral activity; Benzo[f]isoindoles; IMDAV reaction; [4+2] cycloaddition
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