Features of oxa-bridge cleavage in hexahydro-3a,6-epoxyisoindol-1(4H)-ones: A concise method to access acetylisoindolones possessing anti-viral activity

Unusual stereo- and regioselective methods for epoxy-bridge cleavage in perhydro-3a,6-epoxyisoindolones, under the action of the BF3·Et2O/Ac2O system, were discovered. The reaction pathway strongly depends on the characteristics of the isoindolone ring substituents and allows the synthesis of a wide diversity of isoindole-containing heterocycles. The obtained isoindolinones belong to a new class of anti-viral agents possessing a high activity against influenza virus A/Puerto Rico/8/34 (H1N1) in in vitro experiments. © 2019 Elsevier Ltd

Authors
Zaytsev V.P. 1 , Mertsalov D.F. 1 , Chervyakova L.V. 1 , Krishna G. 1 , Zubkov F.I. 1 , Dorovatovskii P.V. 2 , Khrustalev V.N. 3 , Zarubaev V.V.4
Journal
Tetrahedron Letters
Publisher
Elsevier Ltd
Number of issue
43
Language
English
Status
Published
Link
External link
DOI
10.1016/J.TETLET.2019.151204
Number
151204
Volume
60
Year
2019
Organizations
  • 1 Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 2 National Research Centre “Kurchatov Institute”, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation
  • 3 Inorganic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 4 Pasteur Institute of Epidemiology and Microbiology, 14 Mira St., St. Petersburg, 197101, Russian Federation
Keywords
Anti-viral activity; Eliminative ether cleavage; Furan; IRZZBRDKFRXFMY-SFXALEKLSA-N; Isoindole
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